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March 15, 2009

Why it's a good idea to exchange photos before meeting

So. Last week, I responded to a hot CL ad. Mr. Dude and I have since been exchanging emails comparing notes and interests and figuring out that we're very much on the same page and why don't we meet? So we arranged to meet this evening over drinks.

I arrived a couple of minutes early, found a seat at the bar, and ordered myself a drink. I was mostly facing away from the entrance, though turned slightly so I could glance more easily at people coming in. At some point while I was facing away, he entered and, apparently, glanced around and saw a woman who looked more or less like me and concluded it was her, because he joined her at the table. He had a toy with him that had been a running theme in our emails, and put it on the table. I was suitably amused by the mix-up and waited for them to figure it out. They gestured at the toy and obviously had some conversation about it. There appeared to be no mix-up, because he settled in and ordered a drink.

Now, we met on the internet, and far be it from me to be bothered by the fact that he's meeting multiple women coming out of his post. I was put off by the fact that it appeared he was having the same conversation with all the women he was in touch with, or at least two of us, if the same prop worked for both of us. And, of course, I was not impressed with his having made a date with two people at the same time and place! Hello, tacky!

In fact, as it became increasingly clear that they were settling into their conversation, I was increasingly offended. So offended that I wasn't even offended, finally, just gobsmacked. And I had my whole drink, which I could leave, and stalk out, maybe with a brief pause at the table to tell him off briefly. Or I could wait around and see ... did he have a plan for this? Did he think one of us was coming later? Would he glance up and notice me there? So, I decided to nurse my drink and eavesdrop on their date while contemplating the chutzpah involved in this situation.

Minutes passed. They laughed, chatted, chuckled. Meanwhile, I realized that the guy who just came in and sat beside me is someone I met several years ago at a social event and later called to ask out on a date, which call he never returned. I hoped he didn't recognize me; at any rate, he didn't strike up a conversation, and neither did I.

Suddenly, a shriek arose from the table. "Oh my god!" yelled the woman. "We're meeting the wrong person!" General exclamations and startled looks arose, and it was immediately apparent to me that my first conclusion -- that he'd sat at the wrong table -- spot on. Unfortunately, it had taken them longer to sort that out. He turned and saw me (I kept my head down and pretended I hadn't noticed any of this), and made a quick switch to come over and introduce himself. "Let me tell you what I just did," he opened.

I admitted to having observed the slip-up, and we had a good laugh at the whole situation. We had actually exchanged photos before meeting, but the woman did look vaguely like me, and it was dim, and it can be hard to translate photos to real life. We wondered if she and her date had exchanged photos, though, because when he finally arrived, he looked nothing like mine. So, I suppose the moral of this story is that photos are helpful ... but no substitute for speaking clearly when introducing yourself that first time.

December 2, 2007

Don't be desperate!

So, I have this friend. He's a smart, capable, fit, entertaining guy in his 30s. He's great! Except, he exudes that air.

You know the air I mean. It's that air of desperation. It's the air that precedes him when he walks into a room so all the nice women there know to avoid him like the plague, and all the mercenary women perk up and think, "Oh, hey, I can string this guy along for months before he catches on that he's not gonna get any..."

This guy isn't looking for casual sex; he's looking for a serious relationship leading to marriage, and he's utterly miserable about the lack in his life. Seriously, he can't have a conversation without bringing it back to this at some point along the line. It kills me.

Why? Because if he weren't so achingly, painfully, heartwrenchingly desperate, he might have a chance. But I like him, and even I get the willies when he's around women who are potential matches, because I can feel all his clingy little psychic tentacles reaching out with trembling, pathetic hope that maybe... possibly... could it be...?

I want to tell him to chill out and relax, but, of course, that's no help, because, well, he really does want a girlfriend, and unless I have some specific suggestions as to how to chill out and relax, he maintains himself in this incredible downward spiral of flailing desperately, which makes any potential partner nearby flee in horror, which leads to more flailing...

So, listen, I can't tell him this, but I can tell you:

The absolute first step to being hot is not to need to be hot. In fact, it's not to need anything from the stranger you're meeting-and-maybe-interested-in. It's all well and good to need things from your friends or from your partner, but if the first sense I have of you is that you need me, you can be damn sure I'm going to run screaming. And the people who find that hot? Watch out for them. Abuse comes in a hell of a lot of forms.

This friend of mine, he has several great hobbies, which he continually talks about as ways to meet women. It's true that hobbies are great ways to meet new people, but you should be doing them for yourself above all. As long as every act you engage in is oriented toward finding someone to hold you at night, you're going to give off that air.

My advice is this: Find yourself. Make yourself a whole and happy single person. Create a life that is complete and fulfilling to you. Then figure out how to make a space in that will be comfortable and inviting to someone new, who might like to come home with you and spend the night and maybe make a life together, if that's the sort of kinky shit you're into.

June 14, 2007

Keeping my eyes open when looking for someone new

One of the challenges I run into is this: Having a hot hookup makes me eager to have more. It's the "the more I get, the more I want" feedback loop. So I can go a while being focused on other things, and that's great, but then something comes together, I have a great date, and I'm off to the internet to go shopping for more new lovers.

That, in itself, is fine. But the problem is that after a hot date, I want more like that. That's great if my new lover is local and has time in his schedule that matches the time in my schedule, but that's rare. So, now I find myself trolling CL for tall, dark, handsome men with a slight southern accent and who drink Grey Goose and tonic while admiring my ass in just that way. And with big hands. Like that guy I met Monday! Mmm, Mr. Monday!

So, now I'm reading all the responses to my ad through the lens of wanting that particular thing. Which is silly! Because I like lots of different kinds of men, and lots of different kinds of hookups, and of all the criteria to sort on, proximate resemblance to Mr. Monday is really just about the dumbest there is.

Which leaves me trying to read responses with, "What would the sane (i.e., not lustfully remembering) me think about this response?" It's not pretty.

On the other hand, Mr. Monday? Very, very pretty. I sure am looking forward to seeing him again!

April 5, 2007

Fantasies promise much

One of the most fun elements of meeting people online is the excitement of a promising new contact. There are a lot of duds out there, or people who just aren't good matches (guys, that's a good thing to keep in mind when you don't hear back from a woman: there's a good chance that if you'd even gotten as far as meeting, you'd've decided, "Eh, she had promise, but, ultimately, no dice.") but there are also good matches, and you do occasionally find them, or they find you, and that's awesome.

But you don't know early on if someone will be a match or a dud, and hope springs eternal (or for a really long time, anyway), so on first contact with someone who seems just perfect, I often find my imagination running away with me. Just because he's articulate and witty in email doesn't mean that I'll like him when we meet, or, for that matter, the next time he writes to me, but it's the necessary first step. And because I'm an optimist, I like to look at those promising first emails as the door into something wonderful.

This is especially easy for me to do when he describes a fantasy sexual scenario that's perfectly up my alley. Er. So to speak. That makes it incredibly easy for me to get wrapped up in thinking about a) the fantasy b) with him. And that's a good thing from his perspective for obvious reasons.

Now, this is only moderately helpful for you guys out there, because you can't know for sure which of your fantasies might strike a chord with the stranger you're contacting, but if you pick one of your favorites, and you write it well, you'll at least be in good shape for finding someone who shares it. And that, after all, is the goal, right?

February 28, 2007

Kissing and asking

I'm going to get a bunch of details wrong in this post, I bet, because I'm too lazy to verify my memory, and that's not the main point, anyway. Following up on my last post, on first kisses and asking permission:

Back in the mid 90s, Antioch University (I think) decided to deal with a problem they were having with date rape and sexual harassment on campus by making a rule that a person had to verbally ask his or her partner's permission before taking a makeout session to the next level. There was a big stink about this on college campuses everywhere (or maybe just mine) and in a variety of newspapers. Absurd! they decried. How unreasonable!

Well, it did strike me as stiff, but after thinking about it a bit, I realized that it could actually be incredibly sexy to have a partner ask, if he did it in a creative way. No eye rolling or heavy sighing, but if he did it with a twinkle, so that it was an anticipatory rush, or a tease. He could ask permission to take off my shirt, and then not do it, leaving the potential to blossom in my mind. I could ask if I could slip my hand into his pants and watch his eyes react to the idea...

And that's when it occurred to me that asking permission to kiss someone could be entirely sexy. There are the other classic ways of making a first move, and they have a lot going for them, but in a setting where you want to be sure not to make an unwanted advance, and you think there is a not unreasonable chance of misreading signals, I go with the explicit question every time. And it's not even a fall-back. Try it; you'll like it!

February 19, 2007

Advice 101: Only ask for advice if you really want it

Wanna know what I love? I love the guy who asks me for advice and then shoots down every suggestion I have.

Okay, maybe I don't love that so much.

Yes, I've got this here blog, and I have a few opinions every now and again, and I also have that handy little link in the sidebar so people can write me with their questions. Often enough, I don't really have much useful to say about people's dilemmas. Much as I'd like to have all the answers, I really only have like half of them. And it often seems to be the wrong half. (Use a thin coating of soap on the bathroom mirror to prevent fogging. See?)

But I do assume that when someone writes or IMs me with a question, that they, I don't know, want advice. But something that seems to happen pretty frequently in these circumstances is that this person wants me to fix the issue at hand, to give advice that doesn't require work on their part, or, if the problem is that he's having trouble getting laid, then obviously I'm obligated to sleep with him, as that would solve his problem.

Really, people, didn't your parents teach you anything? Complaining is entirely allowed, but don't ask for advice if you just want to complain. And if you ask for advice and then shoot down everything your friends or anonymous internet chick suggest, my advice is that you should expect them to get annoyed and hang up.

February 14, 2007

Make some noise

Oh, hey, look, it's Valentine's Day! I suppose the obvious tip for today would be something like, "Buy your chocolates tomorrow!" But instead, I'd like to say a few words about something that has nothing to do with that, nor with picking people up online. Rather, I'd like to talk about one of my favorite things in sex: noise.

When I first started having sex, I was incredibly quiet. I'm naturally fairly quiet and internal (not that you all would know that about me, so just trust me on that) and my first lover practically had to pry any noises out of me. Part of that was shyness, part of it was the fact that a lot was going on in my head and without practice, I didn't know how to translate that into movements and sounds to clue my lover in on what was good, and part of it was that incredibly stupid desire that many teenagers (and adults!) have that their lover should somehow read their minds to discern how to touch them.

So my lover made me make noise, and after a while, that came to be more natural, though there's also part of me that loves playing in settings where it's important not to make noise. (In fact, one of my favorite places for solo play, when I can get away with it, is on airplanes.) And now, in karmic revenge on his behalf, one of my big frustrations with men is their inclination not to make much noise in bed. So let me tell you why you, whether you're a man or a woman, should make noise:

1. It's hot. Who doesn't get turned on from getting a reaction from their partner? And how do you know you're getting a reaction? Body language and noises, especially the ones that seem involuntary: gasps, moans, shudders, whimpers. Come on, even reading the words is hot.

2. It tells your partner that you like what she's doing. If I'm nibbling a guy's ear and getting no reaction, I'll assume he doesn't particularly enjoy that and move on. I enjoy wandering around a man's body, don't get me wrong, but I'm also happy to linger at the points that are especially interesting for him. But only if he gives me a road map. Moaning when I lick your collarbone is a good way to clue me in to the fact that you like what I'm doing and want more.

3. It tells you that you like what's happening. This is the one that surprised me most when I first started making noise: Hearing myself responding to the attentions of my lover creates a feedback loop that is self-reinforcing. I hear myself sigh, and my brain says, "Oooh, we're really turned on right now!"

4. As a man, if you make noise, you will be in an extremely small minority, and women will love it. Trust me.

January 21, 2007

Personals photos: a tiny detail

I have a very tiny confession to make.

Lots of guys send pictures of themselves with a bunch of friends, and about half the time, I end up wishing the guy sending me the email was one of the others.

It's great -- really great -- to see real life type pictures from guys, but you should definitely be sure that you're the best one in the shot before you send it on.

January 10, 2007

A quick and easy way to sort out most of the fake ads

I've been browsing the w4m ads in the w4m and CE sections for the past week to see what my competition is, and I have to say, I'm not impressed. In fact, I'm kind of amazed that any of you guys are still trying. Kudos to you! Also, are you crazy? I mean, don't get me wrong, I'm glad there are still hundreds of you out there responding to my every post, no matter how vapid (I'm kidding, of course. I never post vapid ads.) But, seriously, are you nuts?

Well, let's assume you are, and that you have a mailbox dedicated to responding to CL ads that you don't mind dumping and replacing every few months when it is overtaken by spam. I noticed a feature of many of the (few) w4m ads that struck me as real:

Real women are picky.

That is, most of the realistic sounding ads listed not only qualities that they were looking for, but characteristics that disqualified some groups of men, in some cases, large groups of men. Most of the super unrealistic ads say things like, "No matter who you are, I'll fuck you!" Is anyone dumb enough to believe that? Come on. But even the vaguely unrealistic ones tended to leave that open. But, by my count (though I'll admit I didn't respond to more than a handful), almost any ad that attempts to narrow the field by specifying age, marital status, experience level, or what have you, is much, much more likely to have a real person behind it.

December 19, 2006

It never hurts to make a little extra effort

I like it when a guy goes out of his way to impress me. Who doesn't, after all, like to be wooed? It's especially nice when it's a surprise, so I'm not, actually, much of a fan of the hallmark holidays. Oh, sure, it's nice to get a little gift on valentine's day from a sweetheart, but isn't it even better when it's just out of the blue, a little, "I'm thinking of you!"?

Yes, I think so, too!

December 18, 2006

Meaning no when you say no

The corollary to last night's post is the other side of things: we need to mean no when we say it, and say no when that's what we mean.

Unfortunately, it can be ridiculously difficult to say no. We're all trained, socially, to be amiable and friendly, and, in general, saying no is not friendly. We don't want to let someone down; we don't want to hurt someone's feelings; we don't want to come off as a bitch or as cold or... whatever.

So, instead, frequently, we hedge. We imply that even though it's no right now, maybe we'll change our minds later, even if we know we won't. We say no with a little laugh to soften the blow. We waffle.

Sometimes, we say no, but it's hard to say no, to reject someone, so upon repeated requests, each tiem, we soften it, until "no" becomes, "oh, sure, maybe just this once."

Other times, we say no and don't mean it. Maybe we want to be talked into something. Maybe we meant no when we said it but were willing to change our minds a little later on.

We are all responsible for this mess. Men, who are most frequently in the position of the suitor, asking, persisting, it is your job to listen to a no, even when it sounds like she may not mean it. There's a lesson here for her, too, after all, that pretending nonconsent muddies the waters for everyone. Women, who are most frequently declining someone's advances, don't say no if you really mean, "Talk me into it." It's not fair to yourself or to him.

And, of course, don't forget that sometimes it's he who says no, and she who persists, and that doesn't really change the fact that no means no. Or ought to, at least.

December 17, 2006

No means no, and you should act like it does, even if it doesn't

Let's say you're meeting a woman face-to-face after having met online. She tells you that it's just a meeting in public, and she won't take it to a private setting that meeting, and you agree.

You enjoy meeting each other and hit it off conversationally. You think to yourself, "I know she said it wasn't going to go anywhere tonight, but maybe..." So, you make the offer to go back to your place or hers. She declines good-naturedly, in a way that makes it clear she's not offended. Maybe she even indicates regret as she does so.

If you are not sleazy, you will leave it at that. You may hope that she'll change her mind, but any further pressure from you on this point makes you a jerk. Why? Because she has been clear, and you agreed to the terms of the meeting from the outset. One proposal of a change of plans indicates your openness to that option, should it become available. Pushing beyond that indicates that you aren't going to listen to me when I tell you no. Guess what that means?

It means that I'm not going to get into a situation with you where your ignoring my "no" puts me in a dangerous or uncomfortable situation. So, I actually appreciate your giving me warning right up front that you're That Guy.

But maybe you're not That Guy. Maybe you just think that this is what you're supposed to do, or that I will forget that you would like to take me home if you don't reiterate it regularly? Maybe you're really, honestly a nice guy and you think that women say no when they really mean yes.

Unfortunately, some women do do that. But here's a question for you: Do you really want to be with a woman who isn't willing or able to make an affirmative choice? And do you really want to be with a woman whose "no" may or may not mean no? Doesn't that seem just a little risky to you?

You're probably a nice guy with good intentions, and you don't want to put a woman in an uncomfortable situation, right? You may think that this kind of pressure is just what's done in these settings, but it's bad news for all involved. Don't do it.

October 30, 2006

Conversational cues: Don't be a doofus. It turns off the chicks.

One of the things I hate to see -- and it's all too common -- is a nice guy whose lack of confidence and social skills handicaps his options for sex and romance.

Last week, I was at a friend's house for a party, and a fellow I didn't know approached me to introduce himself in that purposeful way that told me he was interested not just 'cause I seemed nice but because he thought I was attractive. Great! We started chatting, and another man joined us. Great, it's a party, we're all chatting, and Guy #1 asks me a question about something I'm passionate about, and I launch into talking about it. Guy #2 breaks in with, essentially, "Let me guess your sign!" and then explaining his thinking when it turned out he guessed wrong. (Note: He did not literally try to guess my sign, but, rather, my origin based on my accent.)

This guy, despite sounding like a complete tool, actually seemed pretty nice. At other points in the conversation, he had interesting things to say, but they were rarely relevant to what other people were talking about. If he didn't know much about the current subject, he had to turn it to something he did know about, even if it meant dragging everyone with him to a topic they weren't interested in, or away from one they were. Unlike someone with a more laid-back and comfortable social style, he was not content to let the conversation drift into waters where he had to listen rather than talk.

This was extra-annoying because I really wanted to connect with Guy #1, but, in truth, it would have been annoying at any time. Conversation is a shared experience, and while it's not rare for me to find someone who can go on and on about a topic in a way that's interesting to me, even if the topic isn't one I would normally be passionate about, but it's essential to pay attention to your conversation partners' level of interest and involvement.

So, a few practical notes on this front, if you think you might sometimes steamroll a conversation:

* Watch eye-movements: If the person you're talking to starts the conversation with a lot of eye contact and the more you talk, spends more time looking away, especially to the side or to other people in the room, as though looking for an escape, it may be time to let him or her talk.

* Pay attention to body language: The more I want to escape a conversation, the more I will turn my body away from the speaker. If you're talking to my shoulder, you can be sure I'm finding you annoying.

* Listen: This one is pretty obvious, but, really, so few people do it. If you're actually listening to the conversation and what the other person is saying, instead of thinking of the next thing you want to say and then jumping it with it at your first opportunity, you're going to seem a lot more interesting and engaged. In fact, you may find that you are, in fact, more engaged.

The puppydogging approach of running from one topic of expertise to another only makes you look desperate and clumsy. And we all know that's never hot.

September 21, 2006

Deal breakers in casual vs. committed relationships

One of the dangers of casual encounters, in my observation of myself and friends, is the risk of something casual becoming something serious. Why is this a danger?

In some ways, I'm pickier when choosing a casual partner. I'm much more likely to be shallow and look more at appearance than I do when I'm looking for a long-term steady. And I look less at personality than I do when I'm thinking about the guy as someone I'm going to spend a lot of time talking with. I'm fine with this, and it makes sense to look for different things from different people based on the role they're going to play in my life. Just as I wouldn't wear flip-flops to a formal event, I wouldn't take my casual fuckbuddy to dinner with my parents. Consequently, I'm less picky about my fuckbuddy's conversational skills, interpersonal interactional style and personal habits.

But what happens when I get attached to the casual guy, and he stops being so casual? Then I'm stuck with someone who swears too much to take home to mom and dad or who wears white after Labor Day or whatever.

In some ways, this is a good thing: Maybe I'm too picky, or the limits I put on who I'd Date date aren't as important as I think they are. It's not always bad when life teaches me a lesson, after all. But in some ways, it's a real risk. You won't find me fucking a republican, even just for fun, but my recent vacation fling was a smoker, which is normally a deal-breaker for me. I sure wouldn't want to end up in a steady relationship with a smoker, no matter how hot and awesome he is.

So, this is the sort of thing it's worth thinking about, at least a bit, if you're doing more than one night stands. If you're fully unwilling to think about something long term with someone who X, or if you deeply wouldn't want to be tightly intwined with someone who does Y, you might want to think very carefully about fucking a person who fits X or Y.

This doesn't stop me from choosing different people for one thing or the other, but at least I know who to blame if I make a misstep.

September 4, 2006

Don't invest too much in potential hookups

Hookups are so flukey that it's a wonder any of them actually happen, ever. This is especially true of hookups that you arrange online. After all, if you're horny and she's horny, and you're physically together to start with, because you're at a bar or what have you, the energy you need to get over the inertia of making it happen is relatively low.

Online hookups required more energy to make them happen, since you're probably both comfortable at home while you're making that initial contact. The tendency is to look for something that's going to be hot and easy, and if it doesn't seem like it's going to be hot enough to bother putting on your shoes and heading out to meet, you might not bother making it happen, or she might not.

The vast majority of potential hookups that I start online never come to fruition. This may be because of him or me or circumstances or who knows what, but it's good to be aware that just because you're in touch with a woman and talking about the potential details of a hookup doesn't mean you're actually in the door.

This was a tough lesson for me to learn. When I first started arranging hookups, I would get all excited about this guy or that one with whom I had amazing "chemistry" via email or chat. We'd talk about fantasies and share favorite porn with each other, and I just couldn't wait until we actually got together! Then, of course, things would happen and the communications would peter out, or the dates would keep getting pushed back, or not made at all, and eventually we'd stop chatting and I'd be all disappointed.

Now, I look at this initial flirtation as a thing unto itself. It's not guaranteed to get me laid, but if it does lead to that, we're sharing important information about the things we like. And if it doesn't, well, I've had a fun chat or two with a stranger. And maybe I learned a trick or two along the way!

August 10, 2006

Mixing drugs and casual encounters: is that really wise?

I'm constantly surprised to see people looking for casual sex and drugs on CL and other sites. Maybe it's because my very first hookup was with a cop who told me that he likes to cruise CL for easy arrests, but it just strikes me as a bad idea.

Now, I've never used illegal drugs, and not because I have anything against them, but, really, mostly because I'm lazy and don't know where to find them and was busy being a goody-two-shoes during the years when my peers were getting busy experimenting with mood-altering substances. So I'm willing to assume that I'm missing something really, really hot by not mixing my sex with drugs.

But it still seems a little foolish to post about drugs on a public website, where the person responding might well be into what you're into, but could just as easily be a cop. Maybe I'm missing some magic code that people have, a secret handshake to allow each to prove to the other that they are for real? Still, I can't say I'd trust that in a casual setting.

Ultimately, I'm in favor of people making choices for themselves, including whether or not to use drugs, but given just how crazy drug laws are these days, I remain surprised what people are willing to put into "print".

August 3, 2006

You're not fucking your therapist, no matter what issues you're working through

I will be the first person to say that my little project of casual sex has helped me grow immensely as a person, both in myself and in my relationships, both sexual and otherwise. I've learned things about myself and general social conditioning that I could not have learned another way. In particular, my relationship to my body and to sex in general has improved immensely in the last couple of years, and I'm not sure that would have happened as quickly and easily if it hadn't been in the context of casual sex.

I've also learned, though, that a lot of people are looking to casual hookups to solve some pretty major issues and problems within themselves, from hangups about their sexuality, their kinks, their former relationships, to rebellion against social norms and mores that constrain them, and beyond. I am all for that kind of growth and exploration, and I'm pleased when a lover comes back to me and says, "Hey, that thing you said, that meant a lot to me, thanks."

But I am not signing up to be your capital-t Therapist. Just because we're fucking doesn't mean that I want to help you work through whatever shit it is you're dealing with in a focused way. If you start to talk about how much shame you've had about sex all these years, and I start to steer the conversation away, it would be good for you to let me.

Sure, sometimes pillow talk gets pretty intimate, and there's something about having that kind of conversation with a stranger that's uniquely freeing, but, as with other aspects of casual fucking, it's important to pay attention to whether your fuckee is getting something out of the experience, too. Unlike in a serious relationship, where lovers sign up to help each other deal with their shit, in casual relationships, getting into too much nitty-gritty can sour things quickly.

On the other hand, that kind of conversation can be pretty great. Just make sure that everyone's on board before your lay down on the couch.

August 1, 2006

Sorry, guys, "hi" doesn't get me hot

So, you've seen a great profile on a dating site, and you're sure that you can definitely show this woman the time of her life. But how do you get her attention??

Do you send her a message with the subject "hi" and a body of "nice profile!"? Are you surprised when you don't hear back from her?

Even on those dating sites where women aren't inundated by offers from men, both interesting and not, most women are just not going to waste their time on this sort of thing. At best, when I get a message like this, I roll my eyes and click "delete". At worst, I point my friends to the guy's profile (usually quite sparse if not totally empty) and mock him.

I'm far more likely to respond to a guy who calls out something in my profile: "I see you write a blog! That's cool, I love blogs," or "Hey, casual sex, that's hot!" I'm also more likely to respond to a guy whose profile contains useful information. I don't just care about your location (I'm only interested in local guys, or men who live in cities that I visit for work with some regularity), but also, oh, I don't know, what you're like. The great thing about profiles is that it's a one shot thing for you: you set it up and then you let it work for you! It's worth taking the time to make it good.

This is one of those things that seems so obvious as to be silly to point it out, but I've gotten 3 "hi" emails on OkCupid this week, so there you go.

July 26, 2006

The out-of-town hookup

One of my favorite forms of casual sex (and the reason I forgot to post last night) is the out-of-town hookup. While I'm normally looking to meet people with whom I can have an ongoing casual thing with, when I'm out of town, I'm really just looking for some good, clean, one-night-stand fun, and somehow, changing my MO changes the whole dynamic.

There are a few things that are also different about the logistics of an out-of-town hookup:

First, I'm usually in the place for only one night. This means that the whole process is accelerated significantly. Where, when I'm meeting someone in my town, I'd plan to meet one day and then actually hook up some other day, when I'm out of town, I have one night to work with, so the meet precedes the fuck by only an hour or so.

Second (and this may just be me), I don't usually give myself a lot of time to make arrangements. Often enough, my travel is last-minute, or close to it, so I'm posting maybe a day or two before. This changes my whole selection process, which goes from, "Choose the best 10-15 and whittle down from there," to, "Choose the best three and go with whichever of those is most communicative and attractive."

The out of town hookup also means there's no dicking around (cough) about scheduling. Either he can make it happen on my schedule or he can't. There's no rain check.

It's fun to mix things up, but there are some additional challenges, too. The main one for me is that I'm usually arranging these hookups in the context of a business trip. That means that I need to be sure that wherever I'm meeting my new buddy is a place that won't involve me running into a) my boss or b) my clients. (This raises a point I've been meaning to bring up for a while: what to do if you DO run into people you know while out with a fuckbuddy. And vice-versa. Don't let me forget!)

When it all works out, though, out of town hookups are among my favorite, if only because they're such a great change of pace.

July 23, 2006

Honesty is the laziest policy

I've talked in the past about my feelings on honesty: It's important. From my point of view, it's the right thing to do in most situations, and certainly in a relationship that you want to last, whether on a casual basis or on a more intimate one. Of course, the more intimate you want to be, the more important the honesty is, because, after all, if you're not being honest, how can the intimate relationship really be what it is?

But even in casual relationships, honesty is important if only so that you can feel good about yourself, and, perhaps more to the point, because it's easier. As I've said before and will, no doubt, say again, part of the reason for me to be honest, in general, is that it's a hell of a lot less work. I don't have to keep track of who thinks I've been doing X, Y or Z if, in fact, I've only been doing and thus talking about X.

Honesty comes into play early on: if you're looking for something particular in a casual encounter, being up front with that is good. One of my weirdest hookups was a guy who made like he wanted to be toppy and when he showed up, he really wanted me to push him around. Now, I can get off on either of these things, but, well, I do a lot better when I can set my expectation/anticipation meter to fit what I'll actually be doing.

Honesty counts beyond that, though, too: It's important to present yourself honestly. Aside from anything particular that you say, if your email or ad makes you sound like someone you're not, either in tone or attitude, that almost always comes through (though not always always, obviously) and it will limit your options. If I get that skeevy feeling of "this guy isn't what he's suggesting"... you can be sure I won't be getting together with him.

Do yourself a favor and take the easy road: be honest.

July 19, 2006

Avoid even a whiff of desperation if you want to get laid

I can't tell you how many guys respond to my ads with some indication of how desperate they are to get their hands on a woman. Any woman.

"extremely horny have not had sex in a while"
"I love anything that turns you on!"
"I don't have lots of experience but I hope you'll take a chance on me..."

Okay, guys, listen up. There's no shame in not being experienced, or in having a dry spell. But it's also not the characteristic you should lead with. I don't want to know all your caveats right off the bat. What I want is for you to tempt me with a few savory morsels.

I will certainly want to know your hesitations or possible deficiencies before we get into bed. If you're nervous because you've never done X, Y or Z with a woman, but you want to try it with me, that's not necessarily the problem. But that's never the place to start. Offer me something to pique my interest before you get into the fine print, because if I'm not motivated to get out my reading glasses, there's really no point.

July 17, 2006

Trying for the unlikely match: specialized tastes in sex

You're a boy who likes something unusual. Something kinky. Something just a little bit off the beaten (ahem) path. How do you find the unusual girl of your dreams?

Often enough, the ad or profile you're responding to will give you a few hints as to the type of scenario she's interested in. Is she looking for a tender lover who likes to go down on her for hours? Does she like it rough? Pay attention to what she says. If it's the same sort of thing you go for, tell her that. What I most want in a guy trying to pick me up is someone who gets hot for the same things that get me hot. It does me no good to find a guy who wants to have me dress up like a schoolgirl if that's not gonna get me going.

There's no problem with you saying what you're into if you think there's a chance the woman you're responding to will go for it, too. After all, there's no way to know if you've met your perfect sexual match, that woman who will be happy to paint you with liquid latex and then trace all over it with ice cubes (for example) if you don't say that's what makes you hard.

On the other hand, however, there's no point in writing out that fantasy for the woman who posted that she's only interested in missionary sex with the lights turned off (now that's kinky). Will it hurt you to give it a shot? Not really, but don't be shocked when you don't hear back.

Women who are interested in a variety of things will usually indicate it by leaving some open-ended hints in their profiles or ads, while those who explicitly close doors won't be a good bet for trying those long-shot interests. In general, people who like one offbeat thing are more likely to like other offbeat things. But that's not to say that just because she likes to leave bite marks on her lover she'll also be interested in tying him up, much less dress him like a doll and sing nursery rhymes to him.

It's hard to find people whose interests match up, sometimes, but when you're into something unusual, you have the advantage of looking in a narrowed field, and, no doubt, with less competition in most cases. As long as you're not wallowing in shame about it (unless that's your thing), you'll probably find a good match eventually, though it may take some time.

July 6, 2006

The thrill of the first date

One of the things I like about having casual sex is that I have more opportunities for first dates than I would if I were in one or a couple of long term relationships. First dates can, on one hand, be tiring and wearing, but they can also be invigorating and exciting.

For example, right now, I'm about an hour and a half from meeting a new boy, about whom I'm feeling very optimistic, and I'm completely atwitter. I've decided, mostly, on what I'm going to wear, but I'm fussing about my hair, and you all will just have to take my word for it that I'm not a girly girl who spends a lot of time fussing and primping under normal circumstances. But this fluttery, anticipatory feeling is fun. Oh, sure, it's also a bit nerve-wracking, and about ten minutes before I leave the house, I'm going to have an attack of the I-don't-wannas, but I get off on intensity, and the intensity of pre-date jitters is no exception. And those pre-date jitters are, for me, most intense in anticipation of a first date, or when I know that in this date, something special is going to happen.

This is also a benefit to the guys I meet, of course, since the more anticipatory I am, the higher my emotional arousal is when we have that first face-to-face flirtatious conversation. The more emotionally "high" I am, the more flirtatious I am, and the more open I am to his flirtation, too. So, some of what determines whether I'll take a guy home with me is my emotional state before I even get dressed for the date. If I had a good day, he's more likely to find me relaxed and receptive to his approach. The reverse, naturally, is also true.

There's not, of course, a lot that guys can do to control what happens to me during the day before I meet up with them, but you can help me feel anticipatory about meeting you. Be friendly, relaxed, and comfortable in your communications with me. Don't get into the long, drawn-out email exchanges: after more than 5-8 useful emails back and forth, the likelihood of my anticipation being high is decreased. By all means, avoid extensive one-line email exchanges. If you want to have a conversation with me, ask for my IM name, or, if our initial emails seem to warrant it, my phone number. (You can give me your phone number, but I'm phone-shy and usually extremely unlikely to initiate the phone contact.)

The more I like you before we meet, the better your chances of getting me into bed, obviously, but if you take it too far, there won't be any mystery, and that takes the anticipatory edge off. Tease me with information, but don't overwhelm me with details: I'll want you to (pun intended) fill in the blanks later.

June 26, 2006

Chill out and grow some balls

I often see, both in profiles in dating sites and in posts on Craig's List, people saying, "I can't believe I'm posting this here. We'll tell our friends we met at a bar/party/supermarket."

People, get over it. I swear, even my parents have friends who've met people over the internet, which means that this is no longer shameful, much less weird or secret. If you are ashamed of posting there, don't do it. No, really, it makes you look silly.

Personally, I'd much rather fuck a guy who is up-front and honest about who he is and how he does things than someone who feels like he has to sneak around and is willing to do something that makes him feel cheap on the off chance it'll get him laid/a girlfriend.

June 20, 2006

Why bother filling out a profile on a dating site?

We all have them: profiles on various dating sites. Some sites give lots of questions for us to fill out, while others leave a general "about me" section that you can complete with as much or as little detail as you like. Even those sites with many fields don't usually specify how much you need to say in each one.

I have one profile that I particularly like, and I tend to use it, or parts of it, as a default when I'm starting one on a new site. I can only come up with so many thoughtful things to say about myself, after all. And I can understand the writer's block that comes into play when faced with a whole screen that I'm supposed to fill with scintillating details about myself.

So what's the point?

You should fill out your profile on a dating site because it's the socially acceptable generic letter that so many of you are fond of sending. You know, the one that tells me who you are without telling me anything about why you found me interesting? The one that I pretty much never respond to, because it's so generic and doesn't tell me anything about how you AND I might fit together? Yeah.

But on a personal ad site, this is your big chance to have all that information in one place, where I would expect it to be. And then when you write me a short note to start a conversation, I can look at your profile and learn about you!! This is great, because it doesn't make me feel like I'm getting spammed, it means you don't have to write as much, and it shares actual information between us.

I get lots of pretty contentless approaches on dating sites. When they're backed up by an interesting profile, the chances of my responding increase dramatically. When I get a thoughtful (even if short) approach paired with a good profile ... well, that's golden.

You've gotta give me something to work with, after all.

June 16, 2006

Responding to personal ads: don't lead with your most extreme trait

I've been thinking about cream pie guy, and in particular, Zachary's question as to whether I would let this guy (if he came across as not dangerous) hit me in the face with a pie?

First, let me talk about the general idea of responding to someone's personal ad. The idea, of course, is that they write an ad that appeals to you on some level, and you then respond, hoping to appeal back. You gradually expose (ahem) more of each other until you're ready to hop into bed or have a relationship or whatever it is you both are looking for. At some point in this process, you may want to share a detail about yourself -- perhaps an insecurity, perhaps a kink, perhaps a health issue -- that you know is not the norm.

I recommend that you not open with your most bizarre or extreme characteristic or interest. (I make an exception here for STD disclosure. You should always be up front about that.) But, if you are into a variety of kinky things, and you see an ad from a woman who expresses an interest in kink, you should not necessarily assume that her kink is the same as your kink, or that your most extreme kink will appeal to her. I suggest that you start with what I call mainstream kink: bondage (everybody likes bondage!) or sensation play (feathers and ice cubes) and maybe something more unusual, unless she has specified something already that moves things along a little faster. Especially if this is your first email to a woman, remember that she's likely to be looking for more than just a wild and crazy guy, who might want to cream (pie) in her face.

Now, two notes here: it may well be that cream pie guy was starting with one of his more moderate interests. In that case, he's given me an important piece of information. Additionally, if he's only interested in hooking up with a woman who would let him do this, then he might as well open with it, because if it's a deal breaker, why waste time? On the other hand, of course (and this gets to Zachary's question), I'm more likely to do something strange for a partner who I know and in whom I'm invested than for someone I don't yet know.

In fact, having a partner with a strong interest in something that has never interested me is one of the most surefire ways of getting me to find that thing hot. And, of course, I'm a GGG girl, so unless it actively turns me off, if it's important to my lover, I'm probably going to be willing to try it twice.

As to this specific activity, I'm pretty sure that if I had a partner who really, really wanted to do this, I'd be willing, but I have two small confessions: a) I hate having stuff on my face, especially sticky stuff, so this one wouldn't be on the top of my things to try, especially because b) I've actually had a cream pie-in-the-face experience, so it's not like I'd even get the purity point for it.

June 4, 2006

Your picture speaks a thousand words, not all of them good

One of the most common mistakes guys make in trying to pick up a woman online is that they have crappy pictures. I know that we'd all like to think that we're beyond the superficial is-he-hot level of attraction and interest, but that's bull pucky. I, and every woman out there is just as shallow and superficial as all the guys, and we're looking to pick people up who we find attractive.

Now, unlike in a bar or at the library or in the supermarket, where I can check a guy out, see how he moves, how he flips his hair back, how he gracefully deposits a pound of chicken giblets into his cart, when I'm meeting guys online, my visual first impression is his photograph. Some guys are more photogenic than others, but, really, it's a rare guy who captures my interest enough that I'll go to the effort of meeting him without having a photo exchange first.

In fact, because the two guys I've met without seeing their photos first turned out to be very unappealing, I'm even less likely to try that again now than I was early on in my online adventures, which is too bad.

But I'm not necessarily talking about your looks. I'm talking about what your photo says about you.

If you're a tiny little figure 30 feet away from the camera, your photo is as good as worthless. I can't see what you look like, and I'm now annoyed because I've strained my eyes peering at the screen hoping the picture will zoom in for me. This photo says you don't want me to know what you look like.

If your picture is all grainy and dim, again, I can't tell what you look like. The impression here is that you never leave your house, have taken a bad picture with your cameraphone, and might be a vampire. Not good.

If your picture shows you with stringy hair combed over badly and is also blurry, you're telling me something, even if you don't mean to.

If you want to do the online dating thing, expect to be asked for a picture. And assume that the recipient of the picture will assume that you're sending pictures of you looking your best. Then rethink the picture you're sending in light of what else it might be telling her.

May 28, 2006

Feedback and relationship processing in casual encounters

I'm back! Thank you all for being so patient with my extended vacation. I had a super-fantastic couple of weeks, complete with some possibly life-changing experiences, a whole slew of incredibly hot people, and a couple of firsts. I hope you all had a great two weeks as well, and that your stories will keep rolling into my inbox; I'm quite enjoying reading them!

Today I'm going to talk about feedback in casual encounters. When one is in a relationship, it's clear when you need to give feedback to your partner, right? Or more clear, at least. But sometimes, in a casual situation, I might desire to give feedback but fear that doing so will start to push things away from casual and toward serious and committed. After all, I think to myself, if we're going to have a processy conversation, that looks a lot more like relationship than it does like casual.

On the other hand, sometimes a little conversation goes a long way to making things go more smoothly, or more hotly, or what have you. So, from time to time, I will go against my native avoidance of big, process-heavy conversations (I don't even like them in relationships, though I'm less likely to work hard to avoid them in that context) and bring up a topic for discussion on the theory that it'll make things better.

"Lover," I might say, "as you know, I hugely enjoy fucking you, and I especially like that thing you do with your tongue. But it would really help me to relax when I'm with you if you wouldn't bring cookies to bed with you. The crumbs drive me crazy."

Okay, it's true, that's not necessarily a big, dramatic Relationship Conversation, but in the context of casual encounters, I sometimes feel like any feedback is pushing up against an unspoken rule of "This is working as long as no one has to change anything for it to keep working." That's fine in a one night stand, but if you have an ongoing casual thing, it might well be worth your while to bring this sort of thing up, especially if it'll help make things hotter or more fun for you. To be casual, after all, isn't the same as not to have opinions. Luckily for me!

May 18, 2006

picking up hot fat chicks

Cluechick is out of town for a bit so I promised I throw in a couple bits of "worth what you paid for it" advice in her absence.

Today's topic is: fat chicks. I'm one. Or, if you prefer, a BBW. Thick. Juicy. Zaftig. Plump. Curvy. Round. Voluptuous. Pick your euphemism, I'm a big sexy gal.

Now I'll admit upfront that I have no idea if my experience is typical for other hot, horny, casual-sex-loving BBWs, so this all might be a total waste of bits. But here are a few thoughts on the topic.

- Sex is hottest with a partner whom I find sexy and who also finds me sizzling hot. If you think I'm hot, that is a big point in your favor.
- On the flip side, if my body is not to your taste, that's fine, but then don't waste my time. Seriously, you would think this should go without saying, but there are horny guys who really prefer thin women, but they aren't getting any, so they'll settle for anyone with holes in all the right places, so they cast a wide net. When I detect one of these, he's a goner: my dance card is too full to let people to fill a slot who aren't really into me.
- To set yourself aside from one of those losers, let me know you like my body. If you are responding to a personal ad, you've seen my picture. If you are responding on CL-CE, I've described myself. Saying something specific about your attraction to my body ("I love your picture, especially the awesome curve of your hips. I love a curvy woman") lets me know that 1) you aren't a "holes in the right places" loser, and 2) you have absorbed the fact that I'm fat so there won't be any awkward surprises when and if we meet.
- BUT...there's a danger on the other extreme, too. There are BBW-fetishists who don't so much love women-who-are-fat as they love FAT-that-happens-to-be-attached-to-a-woman. I don't know how other large women feel about the fat fetishists but it is not my cup of tea. As much as I want you to enjoy my body, I want to be a person, first, NOT an archetype, a charicature or a walking flesh-mound. A few well placed compliments are good; going on and on at length about how much you LOVE my body and you want to touch it and lick it and feel my weight on you and grab my fat in your hands and squeeze, not so much -- I'm going to start thinking you don't care what's between my ears, as long as there's plenty on my bones. My fat is just what's under my skin, and not specifically an erogenous zone. If you are one of those guys who (I am SO not making this up) want to fuck my fat...? Move on.
- Don't make the dreaded mistake of assuming that "fat" is an insult. I'm fat, I know it, and I think I'm damn attractive. I don't need to apologize and I don't need you to either. I can't tell you how many conversations I have that go like this: "blah blah blah as a fat chick blah blah..." "Oh, you aren't fat, you've gorgeous?" "Um, dude, I'm fat. You didn't notice? I'm ALSO gorgeous." "You're just curvy. Today's standard of beauty is so artificially thin, you are just where you should be." "Yes, I'm fine with where I am, but where I am is one hundred pounds over the insurance tables, so let's not play word games, okay?"
- One hint that I'm a pity fuck and you are going to be watching my big ass waving at you from a distance. Or, depending on how I'm feeling that day, nursing a broken jaw.

99% of picking up a big girl is just like picking up a skinny one. The other 1%? Well, I think my main squeeze is just perfect that way: he doesn't lust after a specific body type but instead looks to all types of women to find the rare one who can be a treat for his eyes, his body and his mind. And then he lets her (well, me, anyway) know exactly how hot she is on all fronts.

May 8, 2006

Make conversation count when picking up chicks

I try hard not to pull the, "Tell me about you!" card unless I'm really stumped. I know that when I'm put on the spot with no seeding topic helping to crystalize my thoughts, I can end up paralyzed. "About me??" I'll think in a panic. "What about me? How I look? What I read? Where I grew up? My shower routine? What??" Then, I will, as unobtrusively as possible, sidle away from the conversation in search of something less stressful, like directing traffic in downtown Baghdad. Therefore, I'm sympathetic to the guys who freeze up in the face of similarly open-ended queries from me.

I will point out, however, that I only go to the broad and open question section of my trusty getting-to-know-you handbook after more specific questions have been dodged:

Me: So, what do you do for fun?

Him: Oh, you know, I like all kinds of stuff.

Me: Like what?

Him: Whatever, you know! Just whatever sounds good at the time.

Me: [grr]

Or:

Me: Tell me a bit about what you're into!

Him: I like sex.

Me: Oh, yeah? What about it?

Him: Well, it's, uh... sex. And sex is hot, so I like it. Yeah!

Me: Mmhmm. So, what would you say your style is, or what sorts of things get you going?

Him: Hey, chicks, man, they're great. I really like sex with women.

Me: Okay... [backing away]

The early stages of getting to know someone are tough. And to pull it off, both parties have to be willing to share the work. Ideally, you'll take turns asking questions, and when it's your turn to answer a question, you've got to, oh, I don't know, answer the question, perhaps even with actual information.

I'm not asking what you like in bed just to kill time, after all. If you give me the right answer, as soon as we're done talking, I'll drag you to my bed and rip your clothes off (or let you rip off mine). But if your answer makes me want to claw your eyes out with frustration, you can be sure that the only one getting any in my bed that night will be me. And, of course, my trusty Hitachi, which never lets me down.

May 7, 2006

Please, for the love of all that's good, impress me when you respond to my personal ad

I know, I know, the internet is a harsh mistress for you men out there. There are lots of men, and not so many women, and it seems like there's no real way to make yourself stand out in the world of internet meetings. You're absolutely right, and I'll be the last one to say that I can come up with some magic pill that will make your emails leap off the page every time you respond to a personal ad, much though I may wish I had that ability!

Nevertheless, I can tell you that there are things that don't help your cause. Lame or unremarkable emails are ubiquitous, and though I think it's a hoot to read them and see what absurd thing this guy has decided is the way to get me in the sack, they rarely, if ever, garner a response.

I've suggested in the past -- and I stand by this suggestion -- that you have a paragraph of generic email that you can send to anyone you respond to, but that you open and/or close with a couple of lines that show that you're responding to me. Unless a guy sounds incredibly awesome in his generic approach, I won't respond to an email that's obviously designed to be cut-and-pasted to all potentials.

I know it sucks for you guys, but the truth is, if you can't be bothered to put a little personalization into it, I figure that even if I do respond to you, our conversation will fizzle out before we meet, anyway, so why bother?

April 30, 2006

Sort out the spam from the real women in casual sex ads

Look for something unusual about the ad. Does she have something quirky or humorous in her ad? Does she give some characteristic that sets her apart from some generic ideal? Spammers target the lowest common denominator, so if she's setting herself apart or narrowing down her potential audience, that's a good sign.

Look for longer, chatty ads with personality. Spammers don't put a lot of personality in their ads, and they tend to be brief, sometimes only a line or two. Again, their target is as many people as possible, so they cast a wide net, and this tends to lead to a generic tone.

Look for women who sound "imperfect" (i.e., real). If she sounds too good to be real, she probably is. Women who are looking for casual sex are imperfect, just as all women are. If she claims to be 18 and gorgeous, I'll let you guess what the likelihood is that she's for real.

April 27, 2006

Why I forgot to post yesterday: I blame my fabulous glass dildo

I had big plans last night to post about a couple of tips you guys can use to help weed out the spam "w4m" ads on Craig's List, but I'm afraid I got sidetracked. I really can't recommend sex toys highly enough.

A few years ago, I was working in a fairly relaxed office, with some rowdy people, one of whom (the boss of pretty much everyone in that office) was going through a stressful but mostly amicable divorce. She came in one day feeling generally grouchy and out of sorts, and my direct supervisor finally asked her what the heck was going on. She explained that she was starting to feel some of the frustrations of being single.

At the time, I was also single, and in my early 20s, so, of course, I had a suggestion. "Go to Good Vibrations!" I said. "They're just around the corner!"

She looked at me in amazement. She was in her late 40s and had never owned a sex toy. In fact, it had never even occurred to her as an option. "People use those things???" she boggled.

"People don't???" I boggled right back.

She did not go shopping that day, but she did, eventually, venture out into the world to explore her options. The great thing about sex toys, though, is that they're good for when you're alone or with a partner. They're a great way to learn new things that you like, and to explore with a lover.

There's not always room for that kind of exploration in a casual sex context, but when there is, it's totally worth taking, because you never know what tips and tricks you might pick up.

April 24, 2006

Safer sex and other dull stuff

A friend was recently recounting to me her tale of woe with regards to trying to start sleeping with someone new. In the course of the flirtation, my friend commented to her lust-object that she'd like to know what his STD testing status is, and if he knows his partners', she wanted to know those, too. Her lust-object took this badly, and said, "I would never insult my partners by asking them to get tested!"

Upon hearing this, I first laughed and rolled my eyes, but having given it some thought, it's more than eyeroll-worthy; this kind of attitude is actively contrary to healthy casual sexual encounters. Let's talk about why.

First, everyone has different levels of risk-aversion. And, it seems, everyone thinks that anyone who doesn't agree with them is either paranoid or stupid. I'm explicitly not taking that stance. It's your job as a sexual person to decide what risks you're willing to take, and to be open about that with the people you sleep with. It's also your job to protect yourself, and that means asking questions like, "Have you tested positive for X, Y, or Z?" If you don't ask, it's not reasonable to be upset later that your one night stand turned out, oops, to have tested positive for all of the above, but didn't tell you because she was embarrassed or didn't think it was a big deal or figured you didn't care since you didn't ask. So, figure out what's important to you, what level of risk you're willing to take on, and how to manage that for yourself.

Okay, so now's the time where I call someone stupid. "I wouldn't insult my partners by asking them to get tested," is essentially equivalent to saying, "I would never have the bad judgement to sleep with someone with an STD." This is a fundamental misunderstanding of a) people, b) STDs and c) what it might mean for someone to have an STD.

People who have an STD are not somehow different from people who do not have an STD. And they certainly don't look different, so there's no way to tell just by how someone looks whether or not she or he has an STD. So if you think your judgement is good enough that if you're hot for someone, they must be "clean", you're wrong. Additionally, people who have come up positive on an STD test are not somehow bad people. So, saying that inquriing into someones disease history is insulting is... well, let's just say that I'm not impressed with this logic.

If you're comfortable sleeping with someone without discussing diseases and risk, great, that's your choice, and more power to you. But don't mistake your risk-tolerance for some kind of moral high ground or ultra-fantastic interpersonal filter.

April 23, 2006

I like this thing, and it's kind of embarrassing, and is there anyone else out there who likes it, too?

One of the greatest things about the internet is that it opens a world of possibilities for people who like weird shit. Back in the 70s, I have no idea how people who were into balloon-popping for sexual pleasure found other people who were also into it. (These people, I've learned, are called "looners". If this sounds like your thing, I expect you to give a prayer of thanks to the geeks over at Google. I believe their preferred form of prayer is alcohol.) Any wacky thing you can think of, there's a group of people out there on the internet, chatting and sharing their fantasies and helping each other feel a little less alone.

Okay, maybe you're more creative than I am, and you can think of something for which there is no fetish group. I don't know. But I guarantee that if there isn't yet, there will be soon!

At any rate, what this means for all of you out there who are looking to pick people up on the internet, is that if you have a crazy fantasy that you've always been too embarrassed to tell a boyfriend or a girlfriend, you may finds casual encounters are a good way to play that out.

You want someone to tickle you while you fuck? Or you get hot thinking about that thing you saw on a porn flick once, where the woman leaned back on a yoga ball? Or whatever crazy thing you've been too shy to broach in relationships?

Give it a try! After all, what's the worst that happens? Your date thinks you're weird. Big deal!

April 12, 2006

Casual sex and romance do not mix

I like sex. I like romance. And I like sex with romance, and romance with sex. But when I'm picking someone up in an explicit casual sex arrangement, i don't like or want romance. It freaks me out. It makes me think that he's not thinking about things being quite so casual.

If you're doing the personal ad thing for serious dating, by all means, bring flowers to the first date, wine her, dine her, or what have you. Though, to be fair, I should warn you that if you come on too strong too early, that's not going to be good for you, either.

In the context of casual play, though, none of that should come in, especially not early. You may have an ongoing thing in which it eventually makes sense to have a bit of light romance, but that's not a good place to start.

April 11, 2006

Seduce me with your words

It's extraordinarily unusual for me to respond to men's postings on Craig's List or to their profiles on dating sites. It's one of the major downsides of the dating economy, and especially of the casual sex economy, that I, as a woman, can be lazy and still have my pick of many, many men. This is good for me, and bad for the guys, for all the obvious reasons. It's also, of course, the reason I started this blog in the first place.

But there are ads that occasionally leap out at me and inspire me to respond. Whenever I sit down to try to characterize them as a group, though, I get stuck. I can name the qualities I look for, but they hardly set me apart from the things that pretty much everyone looks for, and they're not at all specific: intelligence, sense of humor, good-natured... Who, after all, doesn't want that?

I may be less picky about the personality traits I look for in a fling than I am in looking for a regular partner, but I still am much more likely to get the hots for someone, even for a one-off, if he's more than just a good-looking mimbo.

So, when I'm inspired to respond to someone's ad, it's because he's gotten me hot with the way he writes. Maybe he's got a witty or unusual turn of phrase that catches my eye (or imagination), or he shows that he's more than just a pretty face in the way he presents himself. This is why it's worth spending some real time on your ad, and the benefit to that is twofold: once you have a good ad, you can use it to flesh out future emails you send to people who might interest you, and also, a good ad can be posted more than once, so the hard work is done.

If you can manage to capture my imagination before we're even exchanging emails, you've made a good first step to getting into my bed.

April 3, 2006

The challenge of the introductory email for online hookups


hi angel you look so pretty,really love to be your friend.am joe shmoe,love to have your yahoo id so we have instant chat,mine is joeshmoecontractors@yahoo.com really like to hear from you.please i will be waiting to see your reply.have a great day

Okay, so I'm on a roll with exemplar emails, so I'm going to keep up with the theme today. This email just arrived to my OkCupid inbox.

Here's the kicker for you guys out there: women online get a lot of email, so what you want to do is set your email apart. I've talked about this in the past, but it bears repeating. What may sound like a perfectly fine basic intro approach would be, in the context of 50 or 100 basic intros, just so much uninteresting noise. The bad stuff, like Mr. Shmoe, above, stands out for its humor value, but lots of guys who I'm sure are actually interesting and might be a lot of fun in bed shoot themselves in the foot by not thinking about the context in which their email will be received.

If you're writing to someone on a dating site, they probably don't get completely inundated on a daily basis, but they probably do get at least several emails a month, and she's probably looking for the ones that really shine. If you're writing to someone on Craig's List, you have to do even better, because she is getting inundated, as she'll likely receive more than 100 emails over the course of the first couple of days her ad is up.

Reread your introductory email in that context and imagine you're on the receiving end of it. Does it stand out? If not, think about what might set you apart from the crowd, because there really is a crowd. Just because it sounds good when its on its own doesn't mean it'll do the trick in a full inbox. After all, you may look hot in sweats and a t-shirt, but if you're going to try to pick someone up in a bar, you'll put a bit of extra effort into your appearance before you leave the house. Do yourself a favor and spiff up your email the same way.

The challenge of the introductory email for online hookups


hi angel you look so pretty,really love to be your friend.am joe shmoe,love to have your yahoo id so we have instant chat,mine is joeshmoecontractors@yahoo.com really like to hear from you.please i will be waiting to see your reply.have a great day

Okay, so I'm on a roll with exemplar emails, so I'm going to keep up with the theme today. This email just arrived to my OkCupid inbox.

Here's the kicker for you guys out there: women online get a lot of email, so what you want to do is set your email apart. I've talked about this in the past, but it bears repeating. What may sound like a perfectly fine basic intro approach would be, in the context of 50 or 100 basic intros, just so much uninteresting noise. The bad stuff, like Mr. Shmoe, above, stands out for its humor value, but lots of guys who I'm sure are actually interesting and might be a lot of fun in bed shoot themselves in the foot by not thinking about the context in which their email will be received.

If you're writing to someone on a dating site, they probably don't get completely inundated on a daily basis, but they probably do get at least several emails a month, and she's probably looking for the ones that really shine. If you're writing to someone on Craig's List, you have to do even better, because she is getting inundated, as she'll likely receive more than 100 emails over the course of the first couple of days her ad is up.

Reread your introductory email in that context and imagine you're on the receiving end of it. Does it stand out? If not, think about what might set you apart from the crowd, because there really is a crowd. Just because it sounds good when its on its own doesn't mean it'll do the trick in a full inbox. After all, you may look hot in sweats and a t-shirt, but if you're going to try to pick someone up in a bar, you'll put a bit of extra effort into your appearance before you leave the house. Do yourself a favor and spiff up your email the same way.

March 28, 2006

Let's talk about safer sex and when it fails

You all know I think you should be practicing safer sex when you're out having fun, right? Good. Now, I leave it to you to decide what level of safety is right for you. Some people like to have up-to-date test results, full-body latex, and enjoy scrubbing each other down with hydrogen peroxide before and after. That's great, as long as everyone's on-board and comfortable with your precautions. Other people don't ask about testing and use latex only the first time. That's not the route I'd choose, but, again, if everyone's consenting and aware, all i can say is that you won't be sleeping with me.

But, I'm not here to lecture you about the "right" safer sex practices. In fact, I'm not even talking about safer sex with regards to STIs today. Indeed, I'm thinking about that traditional bugaboo: pregnancy.

Now, I'm in the lucky position of being the one in charge of the uterus, which means that I know what will happen if I have an unexpected pregnancy. For this reason, I don't bother to talk about it with my casual lovers. I take a lot of precautions to avoid pregnancy, and so far, so good. But if, through a stroke of incredibly bad luck, I got pregnant, I know what my options are, and which one I would choose.

But none of my casual lovers does. Because of all the men I've slept with in the last year, exactly none of them has raised the question with me. Guys, this is dumb. I know there's no good way to slip the pregnancy discussion into some hot pre-casual-sex chit-chat, but if it's not something you're thinking about, you could be in for a rude surprise.

For example, a close male friend of mine had a drunken hookup in a bar only to get a phone call 10 months later from the woman who was suing him for paternity. For twins. Surprise!

The men who sleep with me don't know that I'm a freak about protecting myself against pregnancy, and they have no way of knowing what I would choose to do if I were to become pregnant. One guy even tried to fuck me without a condom, I assume he was assuming I'm on the pill or something, but, seriously, this is foolishness.

Even if you are using condoms, even with "perfect use" you run the risk of pregnancy (about 5%, meaning that in a year, 5% of couples using condoms "perfectly" will get pregnant). And "typical use" is even worse (15%-20%). In one of the big benefits of being a woman, I have lots of other options to protect myself from unwanted pregnancy, many of which are more effective than condoms. You guys, though, don't have a lot of options, so it behooves you to consider what you would do if things went unexpectedly awry. You might even want to talk about it with the women you fuck, just for kicks.

March 26, 2006

Let's talk about body language

When I meet a guy for the first time, he'd probably be happy to have a guide to my body language and what it's saying. Since I haven't yet found out a sly and smooth way to give this sort of thing to people before I meet them, I figure the next best thing is to post it here and hope it helps someone, somewhere.

I usually start with a handshake, unless we've been talking online a lot, in which case, I may start with a hug. Neither of these should be taken as particularly indicative of anything, though; pay more attention to how I say goodbye at the end of the meeting.

If I maintain a lot of eye contact when we're talking, I'm enjoying the conversation and feeling very connected with it. The more my eyes are straying -- to your hair, your hands, the pictures on the wall -- the more my mind is wandering. (My eyes always do some straying during a conversation, as do most people's, so this is a matter of degree.) You're probably okay if, instead of looking at your eyes, I'm looking at your mouth.

If you touch me and I smile or blush, you're good.

If you touch me and I give you a pinched smile, or don't seem to respond at all, stop touching me, because I don't like it.

If you touch me and I move away, pay your bill and leave, because I'm about to.

If I touch you on the shoulder or arm, I like you and I'm trying to send you that signal.

If I touch you on the hand or knee, I'm ready to take you home.

If you tell a really lame joke and I laugh, it's probably a good sign, but I laugh easily, so maybe not. If you tell a good joke and I don't laugh, though, it's a bad sign.

If my cell phone rings and I ignore it, I'm not expecting an important call and I think it's rude to take phone calls when i'm on a date. If I take the call without explaining that it's unavoidable, I'm bored and I'm looking forward to ending our date. If I make a call, it's not going anywhere.

When we're saying goodbye, if I hug you, you'll definitely get another date. If I shake your hand, I have to think about it, but probably not. If I avoid shaking your hand by gathering up my stuff, we're not going to see each other again.

March 20, 2006

So, you got stood up. Now what?

It's always exciting to have someone respond to your email or ad, and even more exciting when that initial contact turns into something that looks like it will blossom into a face-to-face meeting, and, if all goes well, possibly more. But, every once in a while, there's the unfortunate stand-up. They're a blow to the ego, not to mention awfully disappointing in the moment (and if you're not disappointed, maybe that tells you a little something about how you really feel about the person you were to meet.) They've happened to the best of us (well, it's happened to me, so that's close enough to the best of us to rope in the whole category, right?)

Being stood up sucks, no question. And it's up to you how to respond. There are two main possibilities: you're still interested enough to try again, or you're offended enough that you're not. If you're offended enough not to want to try to make plans for the future, you're pretty much off the hook. If you want, you can email to castigate her or him, but there's not really much point. Maybe she emailed or called to apologize. You can either accept the apology and wish her well, or you can stay angry and decline the apology. Really, since you won't be having contact with her in the future, it's entirely up to you and how you feel.

But what if you were stood up and you'd still like to meet sometime in the future? The trick is to express your disappointment and anger but be willing to accept an apology if it's forthcoming. You don't want to bend over backwards for two reasons: First, you've been stood up, and you don't want to establish a pattern of putting up with bad behavior just because you're hot for the stander-up (trust me on this one) because, second, that'll make you seem desperate, and we all know that desperate is never hot.

Now, it's possible that your date won't apologize, either out of defensiveness or just plain old jerkishness. If this happens, move on. There's nothing more to be done there. Count your blessings that you found out she was an asshole before you started fucking her.

If she does apologize, though, be firm in stating your disappointment, but accept her apology gracefully. If she's honest and sincere in her interest, she'll be feeling lousy about having stood you up, anyway, and making her feel worse is likely to make her decide that it's not worth facing her embarrassment in order to see you again. If you really push it, she'll decide you're the asshole and she's actually glad she stood you up, if only so it meant she didn't sleep with you.

This is a tough balance, and I don't actually recommend it. When someone stands you up, it shows that she's not that into you, and unless you could as easily have stood her up, and thus have no particular emotional engagement, it's probably best to cut bait and fish another stream. If you think the sex might be hot and there's no particular emotional drama around the stand-up for you, then, hey, go for it. But watch out for a long pattern of this.

Personally, I can't imagine standing someone up who is someone I'm eager to meet or fuck, unless it's due to circumstances completely beyond my control (traffic, public transit strike), in which case, I'm usually glad to have exchanged phone numbers so I can call him and apologize that I'll be late or won't make it at all.

Tomorrow: You've stood someone up, but you really want to try again. What do you do?

March 11, 2006

Does casual sex have a shelf life?

In a comment on The First Time, I wrote, "Casual sex does, I think, have a shelf life, at least for people of substance. I'm curious to see what my timeout is."

One of my readers (who may or may not choose to identify himself here) disagreed with me, saying that he's been doing casual sex for about a decade and doesn't see the end of that for himself. There are a couple of issues at work on this, though.

The first is the question of monogamy. Most people practice it, but not everyone. if you don't practice monogamy, it's possible to engage in casual sex and committed relationships simultaneously. So, yes, when I wrote that I think casual sex has a shelf life, I was thinking from a monogamous point of view, in which, by my thinking, if you're the sort of person who grows in experience, casual sex will eventually lose its appeal, because it is naturally limiting in terms of the depth of relationship you can develop within its confines. In fact, that very thing is part of the appeal of casual sex, and it simply depends on the practitioner to decide for him or herself if that is a feature or a bug.

Let's say, however, that you're in a situation where you can have both casual and committed relationships simultaneously. Even then, I think that many people will not choose to have casual sex forever. I, for example, expect to tired of casual sex at some point, and possibly soon, even if I choose nonmonogamous type partnerships. I wasn't a practitioner of casual sex last year at this time, and though my adventures have certainly changed my point of view on casual fun, I don't expect to find myself engaging in quite the same fuckfest of the last year in, say, five years. On the other hand, I'm more likely to have friendly sex in a free-form, casual-looking way, and I can imagine that continuing over time.

So, obviously, the lifetime of casual sex depends on you.

March 10, 2006

Perfection: the sneaky trap that leads to not getting any

Okay, I was going to post an entry today on a good CL ad from a man and talk about specifics that made it good, but, then, wouldn't you know it, I couldn't find one. So, instead, I'm going to expand on my post the other day and the idea of perfection.

We all fantasize about meeting someone perfect, someone gorgeous, brilliant, wealthy, kind, funny, generous, skilled, and who-knows-what-all-else. Maybe I picture him looking like Brad Pitt or you picture her looking like Marilyn Monroe, but we have these ideas. But the truth is that perfection isn't sexy. One those rare occasions when I've gone out with someone who comes off as more or less perfect, I end up not interested, for two main reasons: First, I know I'm not perfect, and in the face of such polish, I'm sure that I'm just a drab wallflower, and I must not have a chance at all. This may or may not be true in any of those cases, but that's how I experience it, so for my date to be too perfect is a big mistake on his part. Second, perfection is boring. Trying to connect to someone who's all shiny and smooth is like trying to glue a marble to the wall -- there's just not enough texture or surface area on any spot for things to stick.

Because of this, when I don't like someone I'm on a date with, I find myself feeling more and more shiny and smooth, presenting an increasingly bland and unaffected persona. And that then reinforces my feeling of disinterest when I meet someone who comes off as perfect.

What I find hot about meeting someone new is finding the texture, the substance, the character of him. These are the things that I hook into and that really pique my interest. Sure, when I say I want someone who's imperfect, I'm not talking about someone who only showers once a week or who drinks and drives. But at the same time, if you don't let someone see that you're a real person, someone they can connect to in a real way, you're not giving them much chance to show off the same about themselves, and they're likely not to get as interested as you might prefer.

When you're posting an ad, or responding to one, or when you're meeting someone for the first time, it's important to remember that what they're interested in is the person, not the facade. You want to come off as appealing, interesting, hot, sexy, and perfectly imperfect: approachable and human.

February 28, 2006

Think about what you want in a fuckbuddy or partner

In response to yesterday's post, aaron wrote that he used to have a set of criteria in people he was looking for, but after finding several people who fit those criteria but with whom the relationship ended badly, making him question those things he thought he wanted.

This is an excellent point: Often enough, the things we think we want turn out to be all wrong for us. This leads to the womanwho chases "bad boys" and then bemoans the way she iss treated in that relationship. Or to the man who wants only tall, beautiful blondes but finds them vapid and boring after the initial shimmer has worn off.

It's important to think about what you want in a relationship, whether serious or casual. If you don't know what you want, you'll have a difficult time finding it, though, I'll admit, not impossible. Additionally, if you find something, it'll be hard for you to know if it's the sort of thing you're looking for. It's very useful to know, in a general way, what you want.

On the other hand, it's not useful to limit yourself to too narrow a set of options. If you only want a woman between 5'4" and 5'6" with long hair who runs marathons and reads Chaucer, you're limiting yourself a lot. And many of those characteristics may not actually be relevant to the success of your interaction.

So it pays to make note of the things that you like in friends and former lovers. What are personality traits that worked for you? What didn't? Learning what works and moving on from there is a much more successful strategy than banging your head against the wall.

February 27, 2006

Convincing a woman to break her own rules

Every woman -- every person -- looking for a specific kind of relationship, be it romantic, sexual, or some other, has certain rules or categories they want their new person to fit. I've talked about some of mine: age, honesty, and the like. Other women might look for men of a certain height, race, or income level. Some of these state rules are hard-and-fast, and she won't bend on them. Others... less so.

For example, my typical age cut-off is 40. But if a guy gets in touch with me and really shows off his other attributes, but he's 42... well, I'll probably keep up contact with him, because it doesn't pay to be too rule-bound. On the other hand, I don't bend on the cheating issue, because I know that cheating makes me feel yucky.

Additionally, there are lots of categories that a woman isn't stating, but she's hoping to find someone who fits them. These might be things like a certain attitude or approach to life and the world. Or someone who does some of the same activities she does. Or someone with a really kickass view from his apartment. Who knows, right? And among these unstated categories, some of them she's aware of, and some of them just impact how she feels about a guy -- these are those ephemeral-seeming things that just make us go all gooey when we meet him or talk to him.

So, if you're an older guy responding to a woman's who has stated that you're out of her preferred age-range, but you're convinced that, based on her ad or profile, not only is she going to rock your world, but that you are going to rock hers, then your job is to convince her of that. And this is true of any of her stated categories. She says she wants X, and you're Y, but you can tell that this is an outstanding case. What do you do?

First and foremost, don't waste your time trying to convince her that her categories are off or wrong or that you're somehow better than guys who fit her rules. This is insulting to her, and it won't get you anywhere, because she's already made up her mind about what her rules are, and hearing you blather on about how you're a young-looking 50, or you have more stamina than men in her age range because you're vastly younger than she's looking for, is probably going to make her laugh. This also probably won't work because you have to assume the reason for her narrowing her field as she did, and you're probably going to be wrong. (I.e., I don't care how old or young someone looks, so whenever someone tries to convince me to go up a few years by talking about how young he looks, it misses the mark.)

The thing to do is to read her profile or her ad very carefully, see what she's looking for that you do fit, and try to figure out if you can pick up on any of the things that she's not explicitly stating. Then, write her an email singing your own praises. She wants someone to keep her company at the wine bar? Talk about your adventures in wine country as a young man, when you apprenticed with several well-known vineyards. She wants someone who will go down on her for hours and hours? Talk about the delight you take in cunnilingus. If you can inject your email with sincerity and enthusiasm, it'll be awfully convincing.

Go ahead and state up front that you know you miss the mark on whatever category it might be, and then say, "But I'm writing you, anyway, because ..." and knock her socks off with the proof. Don't ignore the rule, don't make light of it, but show off just how fantastically well-matched you are. It may or may not work; you never know which of any given woman's rules are breakable, but if you're going to try, that's your best shot.

February 25, 2006

Another common characteristic that men want me to ignore

In Older men, younger women and casual encounters, I wrote about my frustration with older men who ignore the age range I put in my ads. Sapiophile has called me on some of what I said, and I'll be posting in the next week or so about ways that a guy can reasonably respond to a woman's profile or post even if he doesn't fit all of her criteria. But today, I'd like to talk about the other most common thing that I specify and men ignore.

I don't do cheaters. I don't actually think that I, personally, have a significant moral debt in cases of cheating where I might be "the other woman", but I don't want to get involved in it for a variety of selfish reasons. First, if I'm fucking a cheater, I know I'll think less of him. Since, by definition, I want to be impressed by the people I'm fucking, and feel good about them, this is a bad thing. Second, I would feel dirty knowing that when we finished, he'd have to wash the smell of me off his hands before going home to his partner. Yuck. And third, I'd think less of myself for lowering my standards, and I therefore assume that he, too, would think less of me. True or not, this would impact my self-valuation, and I like to value myself highly, so this is not an exciting prospect to me.

Because of all this, I say up front in my ads and profiles that I won't bother with cheaters. I'm down with nonmonogamy in a variety of forms, but I am vastly uninterested in being involved in a "behind someone's back" sort of scene.

Nevertheless, I hear back from (cheating) married men a lot. This actually seems sleazy to me, because of my feelings about cheating in the first place. (Why would you want to lie to the person you've chosen to share your life with? The truth is, I know it's always more complicated than that, but I just can't get past that hurdle.) Lots of women don't specify one way or the other about the marriage issue, and it seems reasonable to me to approach them, but if a woman cares enough about it to mention it in her ad, it's simply bad form, in this case, to try to convince her. Unlike in the instances of, say, age or location, this one is a personal ethics call, and you ought to respect her desire to avoid that trap.

February 20, 2006

Drinking, drugs, and casual sex

I don't mix altered states with casual hookups. In other words, when I'm drinking, I don't pick up fuckbuddies, online or in person, and when I'm hunting, I don't drink. I don't use drugs at all, but if I did, the same rules would apply. (I'm not against recreational drug use; in fact, I'm generally in favor of it. I'm just a control freak who likes to keep her wits about her and doesn't trust chemicals or the people who sell them.)

A lot of people like to use alcohol or other drugs to relax themselves for a hookup, or to heighten sensations, or to make it more exciting. I have nothing against this, but I also don't necessarily advise it. Here's why:

In general, I try not to regret things I do in my life. I approach this in a two-pronged way: First, I try to make choices that I won't regret afterwards, and second, once I make a choice, I try to frame it in a way that it's a positive thing. Part of this means that I don't decide who I'm going to fuck while I'm drinking, especially because I know I'm a cheap date, and drinking makes me horny. One glass of wine and I'll be edging my chair close to yours. Two glasses and I'll be on your lap. This can be fun, for sure, when I've already fucked a guy, but it doesn't make for the most clear-headed decision-making if I'm trying to figure out if I want to fuck him in the first place.

The cultural acceptance of the drunken hookup is so well-established that even someone as sheltered from the mainstream as myself is aware of the jokes about how if your options aren't looking so good, you should have another drink. Maybe I'm just picky, but I'd rather feel as good about having someone in my bed when I wake up as when I bring them home.

I don't mind if my date drinks, though I am likely to take it personally if he gets snockered before we head to bed. Not to mention, a completely drunk lover is, generally, a lazy lover. Where's the fun in that?

You all know where your limits are, and if you don't, you should. So only you can say what level of high is okay for you. But if you have to get high to have fun with someone new, I'd say that's worth examining a little more closely, and you certainly won't be getting into bed with me.

Casual sex, safer sex, and how to do both

If you're having casual sex, you ought to be up to date on the health risks involved in recreational sex. If you're not paying attention to your health and safety, you're being dumb. Obviously, anyone who wants to be dumb can do that, but... well, it speaks for itself.

I'm surprised how many people looking online for hookups are looking for unprotected sex. This strikes me as quite absurd, but, hey, the great thing about being an adult is you get to make your own stupid choices.

Personally, I don't practice the safest sex out there. I don't use latex gloves, and I only use latex for oral sex some of the time, depending on my partner. I know these are risky behaviors, and I'm willing to take those risks. I talk about the risks with my partners so they can make their own informed choices, too.

It's your responsibility, as someone who has sex, in whatever context, to figure out what risks you're willing to take, and to be open about that with the people you play with. It's also your responsibility to share your safer sex practices with your partners, and to answer whatever questions they have in a forthright way.

I'm obviously not against engaging in risky behavior, but I'm not impressed by anyone who does so out of ignorance and stupidity rather than clearly-considered choice.

February 19, 2006

What to disclose: Who knows what about whom in your sexual constellation?

Let's say you're a casual sex god(dess) and you have people lined up out the door for a chance to get you into bed. Or, perhaps more realistically, just that you have a couple of people who you fuck around with or a regular person and a couple of fuckbuddies. Or, you're polyamorous and have a steady partner but you also like to get some on the side (I'm not blogging on polyamory, so if you're not up on what it is, just fucking google it.) What do you tell your lovers about one another?

There are a couple of schools of thought on this: There's the, "It's casual so no one has to know anything," option. In this take on things, you basically tell people only what you think they need to know and you don't volunteer anything else. Personally, I suck at this, because I hate trying to figure out what people need to know, and I'm basically an open-book kind of person. (You may have noticed.) It doesn't occur to me not to talk about one lover with the next, especially if someone asks a question like, "So, how's the internet sex scene going for you?"

Another option, therefore, is the, "Everyone knows everything," approach. This is easy as pie, because you don't have to worry, "Did I tell Joe about Ed, or is it going to be weird for me to talk about that fun thing we did that I'd like to try again?" On the other hand, it turns out some people don't want to know everything that you're doing with other partners.

Because I'm lazy, and I hate making decisions for other people, my way of handling the question of what to tell my lovers about each other is to ask them: "Will it weird you out if I talk about my other lovers with you?" I explain that my natural inclination is to be totally open about it, that it doesn't strike me as weird when they talk about their other lovers, and that, in fact, I probably want to know, either for safer sex reasons or for my own lascivious imagination. (Picturing my lover fucking someone else is almost as good as an actual threesome! Okay, maybe not that good, but I like it, anyway.)

If someone doesn't want to hear about my other encounters, that's fine, and I can generally rein myself in, but the job then falls to him not to ask me any questions that might elicit information he doesn't want. My theory on questions is that once you ask them, you're going to get a straight up answer, like it or not. So don't ask a question if you don't want the answer.

I don't think there's a hard-and-fast rule about what you reveal or not, but you need to figure out for yourself what you think. If you're picking up people on the internet, you can probably assume you're not the only one they're seeing. Think about what you want to know, and what you're willing to share with them. Be clear about both of these things, and if you change your mind later, be clear about that, too.

February 17, 2006

The drunken photo of you and some chick: do you really think it's sexy?

A lot of the photos I get were clearly taken when the subject is inebriated. This strikes me as okay, especially if you're a party guy, since you're telling your prospective dates something about yourself with your photo. As long as you don't have that slack-jawed, empty-eyed look of someone who's about to make a break for the bathroom, or, in case of a line, the nearest planter, drunk photos are fine. In some cases, they're better than fine, because there's a lot of entertainment to be had with a picture of a strange guy singing karaoke with another guy in a plush turtle suit (don't ask; I didn't).

One thing, however, that I advise against, is the photo of you plus some random chick. Especially if you've done that goofy black-bar-over-her-eyes thing. If you have the technology to make her look like a Glamour "don't", you have the technology to take her out of the picture entirely. If you have your arm around her like she's your girlfriend, it's just kind of weird to send that to a potential fuckbuddy. If she has a black bar over her eyes in a picture of her sucking your cock, not only do I think it's weird, I think you're an asshole to boot.

The best thing to do, if you can, is to have a good picture of yourself without anyone else in it. If you can't do that, you should cut as much of the other person or people (if they're recognizable) out of the picture as possible while still giving a reasonable impression of you. Whiting out the other person's face, or just her eyes, is nothing more than weird. Don't bother.

I'm all for openness in relationships, and I'm no stickler for monogamy, so I'm not saying this because sending a picture of yourself with a woman will make you look like you're cheating or anything like that. Rather, it makes you look like you don't care about the privacy of this chick whose picture you're sending out to strangers.

Also, I don't like it if she's prettier than I am. Call me shallow and insecure, but I hate to feel like I don't measure up. If I think you're going to ding me because I'm not a 10 (and I'm not), I probably won't bother being in touch with you.

Think about what you're saying with your picture. Are you saying, "I will use photographs of you without your permission in the future," or "I look good when I'm three sheets to the wind," or "I fucked this girl before you, don't you feel special?" Personally, I suggest the message should focus, rather, on you, and it should say, "I'm attractive, well-groomed, and will give you a great orgasm if you just give me the chance."

February 15, 2006

What is kinky?

As the saying goes: I'm kinky; you're perverted.

I'm always fascinated by the variety in perceptions from one person to the next. This is true in all settings; it just happens to spring into relief online, where people are more likely to spell out what it is they want, what they think, how things look to them. You can't tell of the woman you're considering propositioning in the grocery store checkout line is into wearing stockings or not, if the guy at the bank is going to go for being tied up, or what have you. And, obviously, depending on who you spend time with, any given activity may or may not jump out as weird to you.

For example, in one of my ads, I said something about looking for "kinky fun". One poor fellow responded that he was into "BJ/HJ/FJ ... kinky, huh?" I, of course, thought that this must be a different set of activities than I thought, because, surely no one is still thinking that blowjobs are kinky? So, I responded, looking for clarification. Upon clarification that, yes, indeed, he did mean blowjob/handjob/footjob. Poor guy.

Just about any wacky thing you can imagine, you can find online. In fact, lots of wacky things I can't imagine are to be found online. But even without dredging the depths for the strangest or most unusual sexual preference, there's lots of room for confusion. Is bondage kinky? It's certainly lost its cache if major hotels are providing cuffs as an option on the room service menu.

Kinky is obviously in the eye of the beholder. If you're looking for something specific, spell it out. And if you want some fun, leave it open-ended, because you're bound to get some surprising responses.

February 11, 2006

Okay, so I'm a snob. Deal with it.

Some people have noticed that I'm a bit of a snob. I snark the net-speak emails I get that replace "you are" with "u r" and I blithely ignore the emails that don't meet my high standards. Aren't there women out there on the net who are less particular in the ways of intellectual seduction? Shouldn't I cut guys a little more slack?

The answer to the first question is: Yes, absolutely. There are millions upon millions of women in the US -- hell, just on my side of the Mississippi and Mason-Dixon line -- who are less fussy than I am, especially about things like coherent sentences and good grammar. Just because I mock these things in conversations with my friends, family, and strangers on the internet doesn't mean that I'm the last word on them. If you'd rather fuck someone who doesn't care about such things, by all means, go for it!

The answer to the second question is: Heh.

The longer answer is also a bit more complicated: I have high expectations, and I'm okay with that. It limits my field, but what's the point in playing in a field you don't enjoy? That said, if I get a great, articulate email from someone who confuses "your" and "you're" or who doesn't capitalize at the beginning of sentences, or what have you, I'm not likely to rule him out for orthographical errors. Sure, I may have doubts that wouldn't exist with someone whose every email is letter-perfect, but I care more about the content than the dressing. It's just easier to appreciate the content when the dressing isn't actively distracting me.

I won't, however, cut anyone any slack on the content piece. You've got to engage my mind before you can even consider engaging my body, and online, the way to do that is through your email. No, you don't have to spell everything perfectly, but you damn well better impress me with what you've got behind those typos.

February 10, 2006

Too tall, too short, or happy medium? Height and the online scene

When I get an email from a short guy, even one that's really not up to par, I nearly always want to write him back, whether he sounds like a good match for me or not, to say how much I like short guys. It's not that I specifically like short guys more than tall guys -- I like tall guys quite a lot -- it's just that I don't sort on height, which, obviously, lots of women do, and I always want to give the short guys out there a boost.

I usually don't do this, because I have this silly little internal filtering mechanism that tells me who I'm allowed to respond to or not. Yes, I know, it's my own filter and if I break other people's rules, I sure as hell ought to be willing to break my own, but that's a discussion for another day. At any rate, my internal filter tells me things like, "You can't respond to that guy with the hot photo because his email blows, and you'll get depressed about it later if you do," or "This guy is younger than you usually go for, but he writes incredibly good email, so you might as well flex on this one." You can see that my filter really focuses on internals.

So my filter tells me, more or less entirely based on someone's writing, who I'm allowed to respond to. And if a guy writes an email that's not up to par, I don't respond. Okay, good enough. The problem comes in because there are categories of men that I know get a lot of rejection for something that's not the reason I'm rejecting them, and I always wish I could send them a note saying, "Hey, your email sucked. I'd totally blow you if you turned me on with your writing, even though you're only 5'5"."

The truth is, there's a lot of fun to be had with a guy who's approximately my height. I have an ex who was more than a foot taller than I am, and I had to stand on a step to kiss him without his help (he was usually quite obliging with the stooping down, but I know he's always happy to meet a woman for whom he doesn't have to stoop), and that had its fun, but also its awkwardness. And there's a little something fun about things lining up just so when I'm standing around smooching on a guy.

So rather than write email to each short-but-still-not-email-sexy guys who sends me mail, I thought I'd write this. Short guys: you're wicked fun. Don't let anyone tell you otherwise. And to my fellow chicks: get over the height thing. There's a lot of fun to be had at all heights.

February 6, 2006

Pretty is as pretty does

Following on the heels of How picky is too picky, there's another complaint that I've heard from another group of guys: this one comes from men who rate themselves, to me, as "okay looking" and who have complained about less-than-stunning women choosing not to hook up with them based on their looks. After all, if she's no looker, she's got no business being particular!

Uh huh.

Like it or not, a focus on looks is something we all have to deal with -- both in ourselves and in our potential partners -- when we're in the hookup scene, or even, more broadly, in the dating scene. Some people are more picky about looks when it's just sex, and some are more picky about looks when it's dating. (Personally, I'm more appearance-oriented for a casual thing, where personality has less opportunity to flesh out my attraction to a person.) But everyone has people they find attractive or unattractive based on their physical appearance, and when you're online, you typically use a picture to make that call. (Thus, having a good photo of yourself is a good idea.)

Then, given that everyone's judging based on a combination of emails and photos, with, in my experience, a lot of weight given to photos, it's no surprise that lots of flirtations fizzle out at the photo-exchange phase. It's also no surprise to me that each person's taste may not match what their potential lovers think it should be.

It turns out that a person doesn't have to be drop-dead gorgeous in order to desire a partner who is. And someone plain may reject another plain person based on his appearance. There's no social rule that says that an average looking woman can't lust only after someone hot (remembering, as always, that "hot" is subjective). It may limit this person's options, but that's her problem, not yours.

Ah, you say, but it is my problem if she's rejecting me because I'm not up to her standards. But, frankly, that still sounds to me like it's her problem. Your problem isn't her, but rather, the fact that you're getting hung up on it. No one's a sure bet, online or elsewhere. She doesn't owe you anything, especially not based on her looks, good or otherwise, so get over it and move on.

When opportunity knocks...

I'm notorious amongst my friends and coworkers for getting frequent and unexpected pickup attempts. What makes this particularly funny is that I don't spend a lot of time in pickup locales. I can count on my fingers the number of times I've been to a bar, and I've never been to a club. I understand that these are fairly traditional places for pickups to happen.

Instead, I get pickups at train stations, libraries, walking down the sidewalk and at professional conferences (note: avoid pickups in professional venues, no matter how boring the speakers are). I don't know why I get these pickups, because I'm not, despite what my friends might tell me, a breathtakingly attractive woman. I'd say I'm solidly in the category of attractive, but not go-out-of-your-way-to-get-a-date attractive. So what inspires these men to throw caution to the wind and ask me out for coffee? The general consensus (among my friends) is that I'm friendly and open-looking. That is, I make eye contact with people and smile.

What does this have to do with the online dating scene? Only that being friendly can open doors. Obviously, you can't easily tell from someone's ad or profile if they are friendly, but you can emphasize your own appeal by finding connections and fleshing them out. The way to do this is to read an ad closely and see what it says about her. Does she write in complete sentences? You should try to do the same. Does she talk about something she likes? You can connect with that. By recognizing her as more than an object, but rather, as a whole person, you can connect with her on that level (or, rather, on those multiple levels), and that will help both you and her to find a good ground from which to make your start.

February 5, 2006

How picky is too picky in the online scene?

I've received several emails from men who have written to complain that the women they've met on CL aren't, for whatever reason, up to these men's standards of attractiveness. These emails never contain a photo, so I can't tell you if they're coming from men who, based purely on the shallow measure of a picture, would normally expect to pick up stunningly attractive women. At any rate, you can imagine how sympathetic I am to these complaints.

If you want to make it all the way to the bedroom by way of online hookups on CL or elsewhere, and you're getting to the point of actual email contact with a woman, and then you are declining her rather than the other way around, then you're in the lucky position of having more opportunities than you need. Be happy with that! But if you're in that situation and you complain about not getting laid enough, then it's possible that you're being too picky.

I define "too picky" as meaning that you are the hurdle that you can't get over in order to get what you want.

There are a lot of attractive women on CL, as well as unattractive women. Many of these women, both attractive and unattractive, may not be to your taste. They may be older than you normally like, or fatter, or taller, or more bald, or flatter-chested, or more avaricious. They may, on the other hand, be just what you're looking for. All of these things are determined by you and your particular inclinations.

I have no problem with people being picky -- men or women -- but I do have a problem with anyone thinking that this means the problem lies with anyone other than themselves.

February 4, 2006

Try asking a few offbeat questions

I've commented that I love it when a new prospect comes up with some creative questions for me, beyond the standard, "How old are you?" and "So what do you do for work?" And, naturally, some of you wrote me to ask for suggestions on these. Now, I'm going to give you a few, some of which people have used on me, and some of which I'm just making up myself right now. I'm not sharing these so you can turn them into stale, overused questions, but to spark your creative thinking.

What's your favorite candy?
When you were a kid, what did you want to be when you grew up?
Is there any popular gift item that someone should never buy for you?
Have you ever broken a bone? Is it a good story? (If it's not, you could try making one up for her.)
Tell me something that you'd share with a stranger but not with your parents.
What's the worst pickup line you've ever gotten? Best?
Where's the strangest place someone's ever tried to pick you up?

(In general, I love questions that show that he's not intimidated or freaked out by the idea that I've flirted with/dated/fucked other guys. On the other hand, these questions can backfire if she's never been at the receiving end of any pickup attempts.)

February 1, 2006

How to tell she's not interested

[Personal note from Cluechick: I will be back tomorrow. Having had a quick skim of Sapiophile's posts, however, I can see that I needn't worry about how to keep things going here when I'm away in the future!]

It's one thing to suss out the clues of lack of interest when you're face to face, and another online. Here are a few things that are likely indicators that your email contact doesn't want to meet:

She never offers to make plans.
She dodges your offers to make plans.
She makes plans but then cancels them.

These all seem pretty obvious, right? But sometimes they may be paired up with the assurance that she really does want to get together and just can't find the time right now, or a series of good excuses, or perhaps just your own desire to make it happen with this person (Cluechick has been the victim of this last one, herself, let me tell you). I recommend a "3 strikes" rule for cancelled dates and somewhat more for noncommittal discussions of possibly making plans. Unfortunately, I have no always kept to the 3 strikes rule, myself, and that's part of why I can recommend it so wholeheartedly!

If you are always the one doing the pushing to meet, that probably means that you're more interested than she is, but that may or may not be a bad thing. I have a fellow who i've been IMing with for a couple of months, who, with his friendly persistence, has finally convinced me that I'd like to get together for coffee. (Note: I said "friendly persistence" not "pushy insistence".)

Many women who are meeting people through the 'net are actually quite leery of meeting for real, and they may not even be aware of their own lack of motivation to make it happen. As always, you need to decide for yourself how much you're willing to wait around, and if it doesn't happen before then, simply cut your losses and move on.

January 29, 2006

Just Say No to Stupid Handles

Our esteemed Cluechick is on the road for a few weeks, so she asked me, Sapiophile, to fill the gap here with a couple entries of my own.

The biggest difference between Cluechick and me: she's much nicer and more forgiving than me. So don your asbestos suits, and gear up for today's topic: names.

"What's in a name?" Juliet asked. Her conclusion: "It is nor hand, nor foot, Nor arm, nor face, nor any other part Belonging to a man." But she's wrong; in the world of the Internet, one's name is one's face. So just as you would not (we hope) show up to a first date with jelly smudged around your mouth, don't wear a stupid name in public. This applies to both handles you select on dating sites, and on chosen email names.

Before I suggest how to pick a good one, let's take a look at some categories of real life bad examples:

Boring: Paul14, NYCguy, mikey1963, SirMark --
this is the best category of bad names. These aren't going to hurt you, but they make you forgettable, which is a bad thing when you are trying to stand out in that hot woman's inevitable flood of responses. (Here's a clue: if the system you pick a name on tells you that yourname, yourname1, yourname2, and yourname342 are taken, that's a hint that it isn't very original.)

Cliche: lonelyguy, looking4luv, BBWluvr22, curiousmale66 -- okay, these may have the advantage of saying more about you than "Joe493" does, but they leave your target chick yawning from your lack of creativity. At least they aren't as bad as...

Stupid: BigCock4U, cum4me, SirHardOne, HornyPig, 9InchesOfLove, hotbod3 -- you might as well hold up a sign that says "I'm a big doofus" as wear one of these names. These names are remarkably popular with the guys and yet...I've yet to find a single woman who finds them appealing, or even funny (beyond a "Haha, what a doofus!") So if you had been considering using "wellhungguy", just quit now, okay?

The very best names are those that are original, say something about who you are, and ideally provide another starting point for conversation. You can't have too many ice breakers.

I just did a quick look around some of the systems I'm on and found some names that appeal to me (or at least fail to turn me off):
- stradivarius (the name of a famous line of violins) - suggests to me education and an artistic bent, maybe a musician
- honeydewmelon - made me chuckle and makes me wonder if he's sweet
- xreipar - no idea what this means, but it looks like it has a story behind it, and I'd ask him in our first email exchange
- TatooedDude - kind of lame but the rhyming is cute and at least it tells me something about him
- cocopocoloco - making me laugh is a good start
- ChaosTheory72 - the name is original enough that I'm guessing '72' is his birth year, not how many guys chose "chaostheory" before him. I could be wrong though.
- LemonDaddy - is that the opposite of a sugar daddy?
- trifecta - this one would have been even better if he's been looking for a foursome

Try to find a name that will be amusing, informative, intriguing or all three. Or at very least, try to avoid being tagged a dork by labelling yourself "StudMuffin22".

Tomorrow's Sapiophile's Cluechick Gap-filling topic: why grammar matters

January 28, 2006

Sincerity: it matters

Yesterday, in my conference, someone brought up the issue of how important it is to be sincere in order to attract clients (no, really, this is my work conference), and I was struck by how true this is for dating as well. (See? Even when I'm working, I'm thinking about you all, my faithful readers. I thought about you while drinking a mojito after work, too.)

In many ways, the online dating scene is, more or less, a matter of marketing. You're the product, and you need to sell yourself. Or you're the institution and you need to attract clients. Or whatever riduculous metaphor strikes your fancy and makes you think of creative ways to make yourself stand out without looking ridiculous or using terms like "synergy" or "value-added".

Sincerity is a good way to make yourself appealing. I like it when a guy is sincere because I like it when I feel I can believe what someone is saying to me. I like to have the sense that his attraction to me is real. That makes it a compliment rather than an act or something that's all for show.

So I spent the afternoon thinking about what someone can do to show that he's sincere, and though I hate to admit it, I'm a bit stymied. I know it when I see it, but I don't know how to describe it and certainly not how to fake it.

On the other side of the coin, I also know when I'm really feeling sincere as opposed to when I'm just putting on a show. And when I pay attention to my internal state, to whether I'm sincerely feeling interest in what a fellow is saying, it tells me about my gut response to him. Sincerity is a clue not just to the person you're interacting with but to you, yourself.

Now that's added value!

January 27, 2006

Looks, shallowness and online dating

I wrote yesterday in How to say no, thanks about ways to pass on continued contact with someone you meet online, and Sapiophile made a useful comment on my interpretation of one fellow's awkward and pointless dance around saying he wasn't interested in me:

He feels guilty for being shallow for not being attracted to you. He thinks he should't be focused on looks, but he is, and all the verbiage is his dance with his own superego. The dance should be done on his own time, not yours.

She's probably right. After all, I, too, have struggled with myself over hitting it off with a guy via email and then finding myself cold and dry after he sends me a photograph. I like to think I'm above that sort of thing, after all. Don't we all?

The truth is, however, that no one is. We all have our likes and dislikes and some of those play out in the realm of appearance.

Personally, I assume that some people I chat with will see my photograph and decide I'm not their type. I'm completely fine with that, because I also assume that people will send me photographs that I'm not attracted to, as well. If the email spark is strong enough, that's sometimes enough to make me take it to in-person, anyway, just in case, but sometimes I just go with the shallow, "Okay, no zing there," response and move on. Thus, in the way that most people think that others generally think the way they do, I think that others must also make a judgement based on my photographs and go from there, either interested or not.

As far as I'm concerned, this is a-ok. We're hooking up online, for goodness' sake. It's not lifelong commitment or picking the next president. Looks and attraction matter, and it's nothing personal if someone doesn't like my looks, just as it's nothing personal if I don't like yours.

If you've got issues with being shallow (or sometimes being shallow), bummer for you. But don't drag me into it!

January 25, 2006

Flattery: an excellent approach

Flattery will get you everywhere.

Flattery is a great way to get a woman's attention, but if you go overboard, it begins to look ridiculous as well as insincere. What do I mean?

One of the fellows who contacted me via Yahoo! Personals started out with a couple of nice compliments on my profile and photographs, and then ramped up to talking about how gorgeous and sexy and brilliant and everything great I am, and before we'd chatted for five minutes, he was telling me he thought I was The One. Either he was crazy or he was lying, and either way, you can imagine my reaction.

Not all insincere flatterers are quite that over-the-top, but in many cases, they're nearly so! Even the ones that go on and on about how great I am begin to be boring before too long.

A bit of flattery is nice, but if you take it too far, it's no longer believable. One fellow said to me in IM, "If I tell you you're sexy, would you hold it against me?" My response: If you say that before we meet, you bet I will!

Furthermore, excessive flattery makes you look like a kiss-up. You don't have to play hard-to-get, but you don't have to crawl after me begging for a scrap of attention, either.

A bit of good flattery to start with is specific to the person you're flattering, and it's reasonable relative to the information that you already have. Something you could write might be:

- "I found you ad extremely provocative and intriguing! I'd love to hear more about what you like to do with rubber bands and chap stick!"
- "Your photograph had me weak in the knees; I can't wait to see you in person!"
- "I'm a sucker for a woman with brains, so it's a good thing I was sitting down when I read your post."
- "You know, the way you write, you sound so hot! You wouldn't happen to be Cluechick, would you?"

(Okay, maybe you ought to skip that last one...)

January 21, 2006

Setting up a first meeting

To follow up on Where to meet the first time after chatting online and Taking things from erotic emails to in-person hookups, I want to talk a bit about the logistics of arranging the first meeting, taking the conversation from online to in-person.

The first thing to keep in mind, guys, is that you want to make it easy for her. If you can go to her neighborhood, so much the better. If you can go to her favorite restaurant or coffee shop, great! Putting up hurdles, like difficult places to meet, or very particular times, is not ideal. If I'm very interested in someone, I'm willing to go out of my way, but if I'm kind of on the edge and he's making it difficult for us to meet, I'll probably throw in the towel.

There was one guy I exchanged a total of maybe 200 emails with -- mostly one-liners -- over the course of a month. He looked attractive, we were into more or less the same things and seemed to be on the same page about what we were looking for -- but he was impossible to schedule with. I tend to be pretty busy, so scheduling ahead a few days or a week is often the only way to guarantee you get a slot in my schedule. He was more of a fly-by-the-seat-of-your-pants kind of guy who didn't want to plan that far ahead.*

That meant that our only possible options were those rare occasions when I had a prior plan fall through on short notice. Okay, fine, that just means waiting a while, which is no problem for me, though I have found that this decreases the likelihood of a meeting actually happening, after a point. So he would drop me an email in the evenings on nights he had free (almost all of them) to see if I was around. If I was, I would respond, and he would commence trying to talk me into going to his house. I had, of course, explained how I prefer to meet in public, but he figured that hormones would convince me otherwise. (They didn't.)

Ultimately, this guy seemed both lazy and pathetic. It appeared that he wasn't getting any, wasn't willing to do much work to get any, and was holding out for something better, which obviously wasn't coming along, oddly enough.

Another thing about setting up a first meeting is this: don't put a lot of pressure on. No matter how hot your email exchange is, the first meeting is the real test. I hate it when a guy talks like it's a no-brainer that we're going to have as much bang in person as we do online, because there's no guarantee that that's the case, and it makes me cranky to have to put on the brakes. Being cautious is to your benefit, too, because, believe it or not, you might meet and decide you don't want to do her, in which case, backpedalling can be awkward.

Remember to exchange phone numbers before heading out to meet. You never know when traffic is going to suck and you or she will run late. It's nice to know that in such a contingency, you can let each other know that you're not standing the other up, just running late.

* A side note about this not-planning-ahead feature: After a couple of weeks, when it became clear that not planning ahead wasn't working well, I took this to mean that he didn't want to commit an evening to me, perhaps on the chance that some better offer would come up between now and then. Needless to say, if a woman gets this sense from you -- rightly or wrongly -- you're pretty much done as far as actually getting her into bed.

January 20, 2006

How to flirt with a cluechick

It's hard to explain exactly how to trip my trigger, because there are a number of ways, and they are all rather individual to the person and situation. As you all know, I like a smart, engaging guy with a good sense of humor, but, really, what on earth does that mean? Who doesn't want those things? Someone who's engaging to me might be offputting to another person, and let's not even go into the ways that a sense of humor can be good and yet still be hugely annoying to any number of people.

One of my favorite things in the world to do, however, is to flirt. I can't begin to tell you how much I love flirting. I like to flirt with friends, with acquaintances, with strangers. I like to think I only do it when it's appropriate, and I never take it to my day job, but nevertheless, I'm a big flirt.

Therefore, probably the number one way to catch my attention in email, IM and -- oh, yes, please -- in person, is to engage me in flirtation. This does not mean that you should give me some blatant come-on, because flirtation is all about hints and innuendos: eye contact, a casual touch on the elbow, a tilted head and suggestive comment. Mmmm, it's a delight just thinking about it!

In email, this means that you should jump on at least one opportunity to make a suggestive remark about something innocuous I said. It may also mean that you don't make a suggestive comment in response to something blatant that I say. You want to mix it up and keep it interesting, right? Flirting is about teasing. In IM, this means that you drop hints, but you don't take it all the way to netsex. (I enjoy a good round of netsex as much as the next person, if I happen to have the time and a free hand, but it's the anticipation that really gets me going and makes me want to take it to the next level.)

In person, well, it's hard to explain how to flirt in person. It requires a lot of attention to the other person's subtle signals. Start slow: extended eye contact is a good one. If the object of your flirtation looks down while blushing, and then re-engages the eye contact, you're good to go. If she doesn't re-engage, that's a bad sign. If she smiles when you touch her elbow or shoulder, that's an invitation for more of the same. If she pulls away, crosses her arms, or leans back... not so much.

Flirtation is like a dance. Sometimes you move forward, sometimes you draw back. The goal is to tease each other into a frenzy, until you can barely keep your hands off each other. Then you're ready to move on to the consummation.

January 16, 2006

Saying what you mean in your ad or profile: hot

Sapiophile writes, in a comment, "Avoid describing yourself as "hot", no matter whether you think you are or not. Instead, focus on those things that you DO believe are attractive about yourself."

This is an excellent point, and one that goes back to the series I had in December on saying what you mean. "Hot" is another meaningless term, right? What I think is hot (hello, bignose!) may be unattractive to others, and vice versa.

In truth, it's not fair of me to criticize someone for describing himself as hot and then turning out not to be, because I have probably been guilty of that, myself. That is to say, I have quite a high opinion of my appearance, but I know that I'm not everyone's type (after all, who is?) This is one of the reasons that I definitely advocate having a reasonably good (and, perhaps more importantly, accurate) photograph of yourself to send to the object of your flirtation at some point in the lead-up to meeting. I do meet the occasional guy without a photo first, but it's always nice to exchange pics first.

One of the things that has been most entertaining for me about what men have said about my photos when I meet them is, "You look just like your picture!" Apparently, this is a surprise. You all won't be shocked to hear that I find the idea of sending an unrealistic photograph self-defeating. Honesty, honesty, honesty, folks. And not just because it's the best policy, but also because, hey, it's easier! Why make your life harder for yourself, anyway?

At any rate, describing yourself as attractive or hot or what-have-you isn't useful at all, because you don't know what the person at the other end of your statement thinks is attractive. Do yourself a favor and smooth the process by being more precise in your self-description. It's good to focus on your strengths, and equally important to be realistic about yourself.

How do not-hot guys get any action?

In yesterday's posts, I was rather focused on the lack of hotness of the fellow in question. I'm sure this caused no small amount of consternation amongst my more average readers (not that any of you is less than fabulous in your own right, I'm sure, but you know what I mean). Let me assure you of two things about hotness:

First, hotness is in the eye of the beholder. Every person has different things they like, and even when going purely on superficial indicators, there are a broad range of tastes out there. I, for example, have a strange and secret fetish for large noses. Not that I seek out large noses, but the faces I find most attractive tend to include large noses. I figure this is evolution's way of balancing out my small nose when (okay, if) I finally decide to settle down with a large-nosed mate and produce moderately-nosed little children.

Second, the more superficial your encounter with someone, the more superficial your hotness needs to be. This is good news for classically attractive yet shallow guys who are looking for casual sex, but bad news for the ones who want a long term relationship. Conversely, substantive but homely guys who are looking for casual sex may well have a harder time, but their significant relationships are likely to be much more successful.

Does this mean substantive but homely guys can't have casual sex? Not at all, but they do have more of a challenge. They just need to be prepared to set it up so their personality is a factor, which it certainly can be in a casual setup just as much as any other. No one's lying when they say the brain is the biggest sex organ, and that's true whether you're having a quick fuck or a lifetime setup. It may take a little more work, but it is totally, totally worth it.

January 15, 2006

Seriously, guys, stop lying

Seriously, guys, stop lying

I swear, I thought this one was really clear. I obviously need to get the word out more effectively. But, listen. Lying in your initial emails with a woman is shooting yourself in the foot. Why?

Because the woman will find out.

Oh, sure, there are lies that, especially in a casual encounter, may well never come out. You can tell me you have a house in the Bahamas and I'll never know the difference. On the other hand, why the heck bother? The lies that are worth bothering with are the ones that will come out sooner or later, and probably sooner.

If you tell me you're hot, great, except, if you're not, and your goal is to meet face-to-face someday, then sooner or later the game will be up. Seriously. I know you guys aren't dumb. Okay, most of you aren't dumb. Maybe a little clueless sometimes, but, hey, that's why I love you! But, truly, I'm confounded on this one.

If a guy tells me he's hot, I'm going to expect him to be hot. And then if he's... well, if he's well below average, he's going to stack up even more poorly in comparison to the expectation he sets for himself in my eyes. Is there some hope here that I'll take him on his word and when I meet him, I'll reset my definition of hot?

For crying out loud, what a waste. Later today: letter to not-hot guy.

January 10, 2006

Why not ask why?

One of the most common responses to my turning a guy down is some form of "But why?"

This is vastly understandable and incredibly pointless, and it drives me completely bugfuck. In my long experience, this response has never gotten me or any of my friends to change our minds about fucking a guy.

Now, obviously, the urge to ask why is driven by two things:

First, you want to know what it is about you that wasn't appealing so that you know about it for the future. As we all know, I am strongly in favor of self-knowledge and growth, so this is admirable. However, it's important to recognize when and where's it's appropriate to gather such life lessons. Unfortunately, though they may be a wealth of knowledge and/or insight, women who have just declined your advances are not a good bet for this.

Second, you hope that she'll say something that indicates that she's got you wrong, so you'll be able to talk her out of it and into you. I'm sure you won't be surprised to know that this is, by far, the more common approach, and the one that I really, really hate. It makes the guy look at least a bit (in the best case scenario) desperate and it puts me in the awkward position of having to either harsh on a guy ("Your photo makes you look like a wildebeast," or "You obviously couldn't eat pussy to save your life.") or tell him that I don't have any particular reason not to sleep with him, but I still don't want to. Since I don't think I need a reason to decide not to sleep with someone, this annoys me.

It's a sad but true fact that guys who don't try to talk a woman into changing her mind definitely won't get any from her, since she's already decided no, but at the very least, she won't be posting to her blog about how sad and desperate you were when she turned you down. Save yourself the trouble, guys, and skip that part of the conversation, because it surely will not get you anywhere fun.

January 7, 2006

Do you have a hook? Use it when responding to personal ads!

Lots of guys want an easy "in" when responding to a woman's ad on Craig's List. Some of you actually have what I call a hook -- that is, a feature that makes you interesting through no real credit to your personality. What are some common hooks? Firefighters, cops, and the like.

A hook isn't something that will guarantee you a response every time, but it's something that can increase your response rate, and paired with a good approach, it's pretty damn golden. In fact, even paired with a pretty lame approach, it will improve your odds.

I have a friend who's fucking an employee of one of her local sports teams. She reports to me that his initial email wasn't remarkable at all, other than the fact that he works for the team, but that little tidbit was enough to get her to respond to an email that normally would have gone into the trash bin. She's not even into sports.

Don't be afraid to use your hooks to snag interest. Not everyone has a good hook, but if you do, by all means, make use of it!

Think about things about you that might be hooks: what do you do for work? You're a computer guy? Probably no joy there, but those of you with more offbeat or romanticized jobs might as well make use of them! What do you like to do for fun? If you just go to the bar with your buddies, that's not very interesting, but if you're into BASE jumping, that might grab someone's attention. Did you grow up somewhere exotic? Be sure to mention your childhood in Timbuktu! Do you have an unusual skill? By all means, include a picture of your impressive tongue origami with your email.

Don't make shit up, of course, but if there's something nifty about you, put it to work!

January 5, 2006

The importance of conversational skills

I keep harping on the need, when approaching someone new online, of treating them like a real person. Why?

It seems to be very easy to forget that on the other side of the computer screen, after you hit "send" on your email or IM, is a person, and often enough, a person you're hoping to get into bed. But especially early in the getting-to-know-you process, they're really more of a mythical being that seems to be answering you through magical means. Treating them like a figment of your imagination is a good way to guarantee they stay that way.

One of the things I look for in my early conversations with guys is whether they actually listen to me. I know, I know, this is classic gender stereotyping, but, guess what? Women do want men who can show interest in us as people.

If a guy asks me if I want to see a picture of his penis, I usually say no, I'd rather see a face shot. 75% of the time, he then sends me a picture of his penis. No matter how promising the conversation has been up to that point, he has just proved that he'd rather send a stranger a picture of his dick than believe her when she says she doesn't want to see it. Either he's way more enamored of his penis than he ought to be or he just doesn't care what I say. Whichever way, he's just proved he's as much a dick as the picture he just sent me.

In general, approaching conversations with people online is like striking up a conversation at a party. You work your way up to the more explicit stuff, though online, that can move a lot faster. Unless both parties are eager to hop into bed, though, having a real interaction is an important part of the process.

January 3, 2006

How guys make the online dating scene hard for themselves

I can't tell you how many men have complained to me about all the fake ads out there and later in the same conversation said that they once posted an ad as a woman to see what it's like on the other side. Mmm, yes, I see the problem, here.

I know that the odds suck, and if you're curious to see what happens to women who post to CL, by all means, pretend to be one and reap the rewards, which include the fact that you're making life harder not only for yourself but for men collectively.

Another thing I've gotten a number of men complaining about is how gay guys put up ads as women to collect naughty photos. Again, I'm somewhat stymied at something insightful to point out here, since the obvious solution is ... (wait for it) ... not to send a picture of your penis on first emailing a stranger. Revolutionary, I know.

Please, feel free to leave tips in the hat as you leave.

January 2, 2006

When should I cut my losses?

In What's the Point, I described the benefits of knowing what you want. But what happens if you meet someone online who seems like a good match but she doesn't seem to know what she wants? She says she'd like to get together but when you try to make specific plans, she dodges them. She responds when you IM her, but she never initiates. She goes hot and cold on thinking about moving the relationship from theoretical to real...

You're dealing with someone who either a) doesn't know what she wants, b) just wants attention or c) doesn't know how to say no.

In the case of her not knowing what she wants, there's certainly a possibility that she'll figure it out, and you may be able to help her along the way by asking questions. I'm sorry to say, however, that lots of people effectively avoid such questions, especially from strangers, by putting on a social script -- things they've heard or thought but that don't actually get to a real answer -- so that technique may or may not get you anywhere.

In the case of someone who just wants attention, there's obviously nothing to be done. I'd like to think that these ones stand out for their narcissism, but I rather doubt that.

And, of course, in the case of someone who doesn't know how to say no... well, this is a huge social problem that lots of women have. It's incredibly stupid, but there may be any number of understandable reasons behind it: she doesn't want to hurt anyone's feelings, or she just never learned the value of "thanks, but no, thanks," or who knows what else? At any rate, there's nothing to be done. Move on.

Unfortunately, there's no good way to sort out which is which, and in any case your best bet is to figure out the limit of your patience and be done with it after that.

January 1, 2006

What's the point?

What is your goal when you respond to a woman's profile or personal ad? Are you hoping that she'll respond and you'll have an interesting conversation? Would you like to get some naughty photos of her to fuel your solo play? Do you want to meet and see if you hit it off in person?

I've gathered, in my time in the online dating scene, that lots of people don't bother to stop and ask themselves these questions. This causes confusion, especially when you have two people who've failed to identify their motivations.

Ostensibly, we're all out there trying to meet people and hit it off, whether for a quick fuck or for the long road to "happily ever after." But, in practice, there are as many reasons for posting or responding to people as there are possible emails to send. You are more likely to get what you want if you know what you want.

So take some time to think about what you're after, both in terms of relationship type, intensity, style, and in terms of the sort of person you'd like to meet. This will help you to be clear when communicating about yourself with new people. Further, knowing what you want will help you to recognize it when you find it.

Self-knowledge: priceless.

December 31, 2005

Saying what you mean in your ad or profile: sexy

No one who's been following this discussion will be surprised to learn that I'm rarely impressed by someone who describes himself as sexy or specifies that he wants the object of his affections to be sexy. Are we playing the obvious game, or what?

"Sexy", like "fun" or "cool", is meaningless. Of course each person wants to hook up with someone sexy, but what's sexy to you may be a huge turnoff to me. The whole point in posting a profile on a dating site or an ad on Craig's List is to catch someone's attention and convince them that you'll be a good match. One of the ways to do that is to explain what you find sexy so that she can say to herself, "Hey, look, here's a guy who wants someone like me!" And on the flip side, you can describe what's sexy about yourself so that that special woman out there who has a fetish for gangly, freckled guys will be sure to write you.

The more explicit and creative you can be, the more you stand out, and the more you stand out, the more interesting you will be. (Okay, that's an oversimplification. There are lots of ways to stand out in a bad way, but if you've been paying attention, most of those should be easy to avoid.) What catches my eye is creativity, and using "sexy" doesn't score that point by a long shot.

December 30, 2005

Saying what you mean in your ad or profile: fat

In my observation, lots of people who don't fit the cookie-cutter definition of beauty like Craig's List and other online dating sites. As such, these areas also attract people who are interested in people outside the Vogue standard, too, so it's not uncommon to see ads from or for transfolks, fat people, handicapped people and others. Today, I'll talk about fat.

There are a lot of different ways to describe one's self or one's desired mate as larger, and each seems to be popular amongst different circles or to carry different associations. One of the most popular seems to be BBW, or big, beautiful woman. (The less common corollary for men is BHM, or big, handsome man.) There's also the straightforward fat, as well as big or larger. Then, of course, you have the euphemisms, which is where things can get a little confusing: buxom, curvy, or thick. I haven't fully figured out thick, actually, but it seems to indicate good proportions on a larger frame. And there's also a smattering of other terms: chubby, chunky, zaftig, rubenesque, plump.

It's hard to know what people are imagining when they describe their desired hookup as any of the above terms: some think size 12, while others may be picturing size 24, and ditto the people who describe themselves in those terms.

Unlike with "fun" or "cool", I don't think there's an easy way to get around these confusions. Until fatness is socially "unloaded" enough that people can list their weight as easily as they list their height, we'll be dealing with workarounds and euphemisms. Instead, my advice is that whether you're a fat chick or someone looking for one, be prepared for people who use the same terms to mean different things.

December 28, 2005

Make your headline relevant to your personal ad

When posting an ad to CL, or writing a profile on another site, you often have the opportunity to include a headline, which should be a quick snapshot of who you are and what you're looking for. Ideally, it'll be catchy enough to garner interest on its own, but at the very least, it should reflect what you'll expound upon in the longer context of the ad or profile.

For my money, relevance is more important than being catchy. Because there's nothing like clicking through a catchy headline that's right up my alley only to find the content disappointing:

Looking for a sexy, smart girl to take out for drinks tonight!

Hi, I'm looking for a sexy girl to take out tonight for some drinks at one of our great lounges downtown (I have a great one in mind). A liitle about me: I'm 31, 5'9, dark/dark, athletic build (work-out often), yes attractive, self employed, [good college] graduate. So why am I posting here, same reason you're looking! Will send pic upon request. I have two businesses that keep me pretty busy and need some relaxing fun! Wanna join me?

Good headline! But the ad? Boooring! And also, what does it have to do with the headline? He doesn't sell me on either why he wants a sexy, smart girl, nor on why one would want him.

Think of your headline as a hint to catch the attention of your audience. It should appeal to the same types of people that your ad will interest, so you're wasting your time and theirs if the headline grabs all comers without appropriate followup in the actual profile. Better to have fewer click-throughs but from actual prospects, and that's where a good headline comes in.

December 27, 2005

Saying what you mean in your ad or profile: fit

Ahh, the ongoing bugaboo on appearance. Let's just take it as a given that when looking for a date, a mate or a hookup, we all want to find someone who's attractive to us. Let's also take it as given that each person has different "types" who they find attractive, and I'm not really in the business of scolding people for their tastes. Great.

Lots of men say, of the woman they're looking for, that she should be "fit". I always assume this is social code for "thin" or, at least, "not fat". This is silly. Fit is orthogonal to fat. That is, they're not on the same line, and that means that you can have both or neither or one or the other. Fit is not, after all, a body type but a condition. If what you mean is that you want someone who can keep up with you when you hike Mt. Hood or ski the Alps, then, yes, you want someone fit (and you may want to specify just how fit you mean). If, on the other hand, you want someone slim, just come out and say it.

December 26, 2005

Saying what you mean in your ad or profile: fun and cool

In many social interactions, we use keys and codes to hint at what we mean without actually saying it. This usually works because we tend to spend time with people who share a common vocabulary. But when you're surfing the web to meet new people, that shared language doesn't necessarily apply.

This means that when you specify the kind of person you're looking for, it's worth taking a bit of time to spell out what you mean rather than rely on words that may mean significantly different things to different people. Some of my favorites of these are "fun" and "cool".

When I say I want someone fun, I mean someone who can keep up with me in conversation, will come up with some wild and crazy thing for us to do on a moment's notice (an impromptu skinny dipping outing? a trip to an amusement park?), or will enjoy the same sorts of movies I do. Someone else looking for someone fun might want a companion to the museum's latest show or a buddy to catch the local team's showing down at the neighborhood sports bar.

Similarly, cool, to me, means someone laid-back, who shares some of my important opinions, and who will like my friends. To you, a cool person may be wearing the right clothes or reading the right books.

So to say that I want someone fun and cool isn't useful, unless I spell out what that means. Hardly anyone thinks they're not fun and cool, at least in certain circumstances, after all. It doesn't hurt anyone not to spell it out, of course, but it'll save a bit of time and confusion, and it may help to target your ad or profile to the right audience in the first place.

December 20, 2005

Come up with creative questions

When you're meeting new people online, you answer all the same questions again and again. I've fantasized about making up an FAQ to get that sort of thing out of the way, but it seems a little antisocial. So we go through the basics with each new person: What's your real name? What do you do for work? What's your living situation? What do you do for fun? yawn

Every once in a while, someone jazzes things up by asking an offbeat question, and I love that! It indicates to me that he's creative, can get out of a rut, and he's willing to be a bit funny or goofy. I'm sure some women don't like goofy, but I'm not among them.

How many marshmallows can you fit in your mouth at once? What's the grossest thing you've ever eaten? What's the longest you've gone without sleep?

Whatever you're asking, a surprising question can shake the conversation out of the autopilot realm and back into actual, interesting interaction. This, on those rare occasions that it happens, is enough to make me sit up and take notice. I like that.

December 19, 2005

Why it pays to be selective in your personal ad desires

At least a couple of times a week, I see a man's CE ad that says something along the lines of, "I don't care what you look like." This is sheer stupidity talking. Here's why:

First, you're lying. Everyone cares about looks, to some degree or other. You may have different tastes than many, you may have tastes that are broad enough that almost every woman in the world could be attractive to you, but that's different from saying that you don't care what your lovers look like. Anyone who disagrees with me is welcome to comment or email, but unless you make an extremely good case for yourself, I will think you are lying.

Second, and perhaps more important, this is not the way to make yourself appealing. "I have no standards," is not sexy. At least part of the fun of a random hookup is knowing you can land someone who's worthwhile and who thinks you're worthwhile. That doesn't mean you both have to be moviestar gorgeous, but it does mean that you each judge the other to be interesting and appealing enough to bed. For me, someone who uses no taste in discerning who he sleeps with will, ultimately, make me feel yucky for bedding him. As I hate that feeling, I don't fuck people who give me the sense that they could be just as happy fucking anyone wandering around with a convenient hole.

Selectivity is a compliment to your partner(s). It's not about being snooty or rude, but rather, understanding and appreciating your own individual tastes. If you have a broad range of attractions, great! More power to you -- you're in a much better position to take advantage of opportunities than is someone who's extremely particular. But don't put down your potential partners in the process.

December 16, 2005

All is not lost: going from online to in-person in 10 easy steps

You know what I love? I love when a guy:

1) Responds to my ad with an email that's clear, coherent, engaging and 2) includes a g-rated picture. When I email him back, he 3) engages in an interesting email exchange long enough to 4) make plans to actually meet. Once we've made plans, he 5) doesn't cancel them at the last minute and 6) actually shows up. While we have coffee (because he 7) didn't insist that we have to fuck the first time we meet), 8) our conversation flows nicely, we both get a chance to talk, laugh and get to know each other. 9) At the end of the evening, we both agree we'd like to see each other again and 10) he emails me after the date to confirm that he'd like to see me again.

Yes, when this happens, it makes cluechicks happy.

Having an IM conversation with a prospective date

On Monday, I reviewed Yahoo! Personals, and not particularly favorably. The most interesting thing about having a Yahoo! profile, and the reason I haven't deleted mine, is that even if you don't pay for the service, if you're signed into the Yahoo IM system, people who like your profile can IM you. It sets up a separate IM profile based on your personal profile, so it's not obvious to the people who see your profile who you "really" are.

Naturally, however, this leads to a whole additional set of advice for men striking up IM conversations with women they don't know. Here are a few tips:

1) If you're starting a conversation with me, it's because you've seen my profile, which includes pictures and information about me. Please, for the love of all that's entertaining on the internet, don't pull the, "Hey, baby, what's up?" and expect me to be instantly fascinated by you.

2) It's especially useful if you start the conversation by saying that you saw my profile, what caught your eye about it, and either giving me some information about you or giving me a link to follow to read your profile.

3) I swear I'm going to maim the next guy who starts a conversation with me with a "buzz". This is a function that causes my IM client to make a loud doorbell noise, and it does, in fact, get my attention. But it's extremely intrusive and annoying. There's no need for this -- most people have their IM clients set up so they get notified of messages, and if they don't, it's probably because they don't want to be disturbed.

4) An IM conversation is not an entitlement to my time. I step away from the computer on a regular basis, or I may be working and need to focus on a task. Sending repeated "Are you there?" messages does not impress me. I'll get to you when I have a moment, and if I don't, I've probably left the computer for a while. If you need to leave, you can say something like, "Sorry you had to step away! I hope we can chat another time."

December 15, 2005

How to respond to a woman on casual encounters

We all know that a man's odds of hearing back from a woman who posted to casual encounters are slim to none. For this reason, it's a good idea not to get too invested in your emails. I recommend that you don't agonize over each word, each turn of phrase, how to make every last thing you write be perfect. If you spend half an hour sweating over how to win this chick's heart, then it's going to be very hard on you if you don't hear back from her. It doesn't do to get attached before you even know her name.

How does this jive with my admonition to personalize your responses? Am I reversing my prior statements and encouraging the generic bulk-style response? By no means.

I suggest that you have a paragraph or two about yourself that you can cut and paste (or, if you're not the cut-and-paste type, a few things you can toss off in a conversational email without having to think too hard about it), and then write a personalized opener and closer that shows you read her ad and are interested in her, not just any woman who might have posted (even if you're interested in any woman who might have posted).

Don't take more than ten minutes in responding to any ad. Think of it as a conversation on the subway -- you have just a few minutes to strike up a conversation and find a connection before you arrive at your stop. Your goal is to get the number and fill in the innumerable blanks later, so don't get hung up on it until that opportunity arises.

December 13, 2005

The power of persistence when chatting up a woman online (and the danger of desperation)

Yesterday, I posted about frequency of posting ads on Craig's List and the importance of avoiding the scent of desperation. This evening, I'm going to talk a bit about persistence when responding to an ad, while still avoiding seeming desperate.

As I've discussed in the past, women who post to CL get a massive quantity of responses. This can make it difficult to appreciate each one. Furthermore, the bulk of them come in the first day and evening, with another, smaller bunch, the next day. This means that some responses -- even good responses -- fall through the tracks.

The approach I'm about to describe is one that you should not abuse, but it can come in handy. If you respond to an ad for which you think you're an excellent match, and you write a really killer email as soon as you see it -- in the first day or two it's up -- but you don't hear back, it may be worthwhile to return to it a few days later and write a short, polite note saying something like, "I responded to your ad the other day, and I know you've probably been inundated by replies! I just wanted to drop you a note to reiterate my interest and hope to hear from you!" Don't put a lot of pressure into it, don't write an email a day until the posting goes down, don't assume that this will be the magic key into the door. However, it can make you stand out, and if she liked your original email but it got lost in the shuffle, this gives her "permission" on the social level to respond even though it's been a few days.

(This is something I always wonder about when I have a full inbox: it's been 6 days since a great guy responded to my ad, and I just never got to writing back to him... it just seems awkward to email him at that point -- he probably doesn't even remember my ad! But of the three times a man has given me a gentle reminder, twice I was glad to get that nod. and the third time, it wasn't a good match, but I didn't mind the poke.)

This can also be a good technique if you heard back from a woman once, but then after responding to her email, you never heard back from her. Again, you may have gotten lost in the shuffle, and it could help you to write another email a few days or a week later.

However, if you do use this technique, I can't emphasize enough the importance of prudence. Do not -- I repeat do not -- overuse this. It's very easy to get pegged to the desperation scale, and desperation is best avoided, not only because it looks bad but also because it is bad. When coming at any endeavor from a place of desperation, you're automatically operating from weakness. Don't do it!

December 11, 2005

Show off when you respond to a personal ad!

When you respond to my personal ad on Craig's List, or to my profile on other dating sites, what I want is for you to show off and convince me that you're awesome. I don't want a lot of apologies or caveats, a bunch of foot-shuffling and hemming and hawing. I want you to tell me who you are and why you're the man for me.

What this means is that, first and foremost, you need to know who you are, so that you can then convey this to me. If you can't do that, there's not much of anywhere we can go.

This also means that you should have a good sense of what you're good at and why that might be appealing to me, based on my profile or ad. And then you should be able to show this off in a way that's confident but not arrogant or off-putting.

Don't be cocky, but be solid. Don't tell me all about your shortcomings, but don't lie about your strengths, either. Give me a piece of who you are and make it real.

December 9, 2005

A couple of ClueChick's pet peeves

The word is "come" not "cum". This one is fairly inconsequential, and all it does is dampen my mood, if your post or email is otherwise hot. Also, I seem to be increasingly in the minority on this one, but nevertheless, I get a little tingle when a guy gets it right.

The word is "discreet" (showing prudence or self-restraint) not "discrete" (consisting of unconnected distinct parts), and ClueChick is, unsurprisingly, neither. Also, if you say in your post that you're looking for discretion, I will assume you're married. If what you mean is that you don't want to bring your fuck fuck pal to the office, you may want to rephrase it because all the cheating married guys out there have ruined the term for you.

What day should I post my personal ad on casual encounters?

As today is Friday, let's talk about timing of your casual encounters posts.

Since Craig's List boards put up posts within minutes of their being submitted, and then displays the most recent first, your timing impacts your visibility. When I have a lot of time to browse through the listings, I may click back to read three or four pages of headlines (there are 100 per page), but if I'm in a rush or just curious to see if something spectacular will catch my eye on first blush, I probably will only read the first page.

This means that you should think about the timing of your post in order to garner the most visibility. Casual encounters, in general, gets less traffic on the weekends, if I judge the response rates to my weekend posts correctly. Especially Friday and Saturday nights, unsurprisingly, far fewer people are surfing the personals boards -- this is obvious, right? But even during the day on weekends, I find that things tend to be slower. People spend less time in front of their computers on weekends, and by the time Monday rolls around again, your ad may be two or three pages back when the sweetheart of your hopes and dreams is avoiding her work and browsing over to see what's tasty in hookup-land.

This is an issue for women as well as men, but, as usual, less so, since there's a search function that allows people to search for any w4m ad (or any m4w ad, either, though that's significantly less useful) as well as particular keywords. (I suppose I should talk about keywords in a future search, eh?)

Some men (and probably women, too, though I browse those boards much less frequently, so I'm less familiar with them) will post the same ad every day for several weeks. You can do this by deleting the previous ad and reposting it. I do not recommend this. My friends and I who browse CL get a huge kick out of this, and give these ads nicknames and would not be caught dead responding to one of them. It's fine to post an ad every day, but you'll do yourself a favor by varying it each day. This may lead you to appeal to a broader audience, and it will certainly leave you in the running at least slightly more with women who are frequent surfers of the board.

Week days are fine options, but they're busy, so your ad will get pushed down more quickly. Think about what time of day your fantasy partner might be surfing around: Is she an office worker who might be bored around lunchtime? Or perhaps she likes to get a bit of late-afternoon titillation before heading home? Maybe you're more of a night-owl and would like to find someone who stays up 'til all hours. Obviously, timing is no guarantee (just as there are no guarantees at all in this setup), but by considering your timing at least partially, you can improve your chances a bit.

December 8, 2005

How to respond to a Craig's List personal ad

Obviously, there are as many ways to respond to a CL ad as there are people to respond. And, obviously, in many ways, this blog is a long answer to that short question. But tonight, I'll share a few quick clues:

1) Be real. Talk about who you are and why you're a good catch, but don't, for the love of all the porn on the internet, make things up about yourself, especially if it'll be obvious down the line that you did.

2) Assume the person on the other end of the line is real. If you're bothering to respond, you should do so with the assumption that it's all on the up-and-up. I can tell when men respond to my ads with junk, and it makes me think they don't think enough of me to try to make a real effort. This does not impress me.

3) Try to write a conversational email that will show off your sparkling personality. I often harp on grammar, spelling and punctuation, but errors in any or all of these fields will fade into the background if the content of your email shines.

Broaden your approach when posting a personal ad

In Focus your email, I discussed the importance of being specific and personalizing your emails to the ads you're responding to. Today, I'm going to talk about broadening your options.

Some people have extremely specific desires: "I want a beautiful woman between 5'8" and 5'10", with long blonde hair and graceful fingers who likes to lick whipped cream out of her lovers' navels while watching ER reruns on Bravo." (I made that up, but you know what I mean.) Most people, however, aren't quite so specific. In fact, some of you out there have fairly broad tastes in broads. If that's the case, I suggest you make a point to say that in your ads when you post them.

That is, if you're attracted to women of all sizes, say so. If you like women with a variety of different looks, mention that! But a word of advice here: Don't say, "I don't care what you look like." First off, that's never true. And secondly, no one wants to be with someone who has no sense of taste.

If you're interested in women of all ages, you can mention that, too. As a side-note on this one, I see a lot of young guys take this approach, with a pretty firm focus. I have no idea if narrowing the field into specialized type searches is successful, but it's certainly worth saying when you're interested in something out of the "mainstream".

If you're looking for something very specific, say what it is, so that you and others don't waste time on a match that isn't right. If, on the other hand, you're open to any number of things, either in the woman/women you meet or in the situation you hope to arrange, then you should offer up the ends of the spectrum that works for you.

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