ClueChick: real clues from a real chick

Last month, I received this query:

I've had some fun with dating sites this year and moved onto trying to pick people up in the real world. Had successs on the two times I've tried - once was a friend of a friend of a friend in a pub and once picking up someone behind the counter of a shop.

In both of these, I had a the chance to make chit chat before I asked them
out. Easy and fun!

For my next amazing trick, I want to try meeting people who I only see for
milliseconds at a time - waiting for the lifts or in busy coffee shop. Hard
places to strike up any kind of conversation.

Do you think this is too direct:

Hi, can you tell me what your name is?
Uh, huh. My name is XXX. Are you a scary lawyer?
Thought so. Would you like to have lunch/dinner with me?

Or better to try and create some chat first?

I would love to have something insightful and brilliant to say, but I really don't. Mostly, I think this is a great idea, and I'm certainly getting a kick out of thinking about it!

Pros: It's playful, fun, lighthearted, and you don't end up spending a lot of time or effort on any given attempt before taking the dive and seeing if it goes to a date-like event.

Cons: It's pretty much a snap-decision sort of issue, so your personality (assuming you have one! which you seem to) doesn't have a chance to shine. I'm guessing that you're reasonably good-looking, though, if you're considering this sort of approach, and that will obviously help. Good grooming and a confident carriage also, obviously, are key here.

I'm guessing you'll get turned down a fair amount, but I wouldn't be surprised to hear that women took you up on this more often than one might expect on first blush. I definitely want to hear how this goes for you!

Posted by ClueChick at 9:34 PM | Permalink | Comments (2)

More backlog in readers' questions:

To start with, I'm a 20 year old virgin. I've made a few postings on the CL CE section in my city over the last two months with little luck. I've tried posting ads that mentioned I was a virgin, and a couple that didn't. For the most part, I usually don't get any responses (from women, at least) which I suppose probably shouldn't surprise me, given the over 50 to 1 ratio of men and women.

Oh, boy.

Okay, so, CE is great. And it's especially great for people who have unusual predilictions, interests, leanings. And it's not inconceivable that someone who has an interest in virgins would be looking there. But it's not likely. And it's especially not likely that the person looking for virgins will be a woman.

Here's the thing: Our culture has a weird hard-on for female virginity. There are plenty of stories about the deflowering of this woman or that one, and the whole bloody sheet ritual that could be, for all I know, myth and legend, but it's still part of our zeitgeist. Firsts are always a big deal, but few firsts are built up to the same impressive, overblown status as the first time a particular pussy meets a cock. Especially if that cock already has a few miles on it and knows what it's doing. In the mythos of our sexual culture, the man should know what he's doing, and he should share his sexual prowess with the inexperienced young woman.

This puts young, inexperienced men at a distinct disadvantage. While not all women demand that their lovers know what they're doing, most do, and few want to deal with what they may perceive as a training exercise. After all, many of us have had to lead even experienced lovers to the promised land. Why would we want to start from scratch?

Now, don't tell me all the good reasons there are for taking a young lover who I could get started with before he has any bad habits. I know there are good reasons to do so, but I also know there are good reasons to avoid it, and, ultimately, the thrill of the first doesn't get me over the hump. And I think that's likely to be true for other women, too.

On another note, as you may imagine, I'm not particularly one to romanticize sex, but I probably wouldn't suggest a casual encounter for one's first sexual experience, either. I have plenty of friends who had that experience, and they liked it, and they're all healthy and happy now, so I certainly wouldn't say my take on this is the only good way to do it, but I'm glad for myself that my first sexual experiences were with people I was dating.

If you're convinced that you want to lose your virginity through the facilitation of the internet, I suggest that you not advertise it as such. Don't lie and make like you know all there is to know about sex, because, frankly, you're sure to embarrass yourself. I don't know how, but it'll happen. I won't tell you the stories of the things I look back on from my early days having sex that make me cringe. Let's move on.

The thing about virginity is that it seems like a burden when you have it, but we pretty much all get rid of it eventually, so don't sweat it too much. Get out there, have fun, and the sex with come in good time. Probably once you've given up feeling desperate and settled for feeling resigned.

Posted by ClueChick at 2:04 AM | Permalink | Comments (3)

I have a bit of a backlog of questions from readers, which I'll try to work through in the next couple of weeks.

I read something on your blog that leads me to believe that you don’t like cheating, yet apparently you have main squeeze and you sleep around. Do you consider that cheating or do you have another definition? This is all new to me since I was married and monogamous forever, but I am not interested in going back to that. Soooo how do you have a main squeeze, and still fool around without someone getting hurt?

You're right; I don't like cheating. In general, I find it foreign and questionable. I understand that there are lots of situations where cheating is the lesser of the available evils, but I have a hard time understanding how people end up in situations where that's the case. Honesty is important to me (though I'm not fanatical about it), and I prefer to involve myself with people who are living basically up-front lives. Furthermore, I am continually baffled at cheating people's openness with strangers about their status while being deceptive with the person who is, in theory, the person they've chosen to spend their lives with. But, hey, I'm also baffled at people's fascination with American Idol, so, big deal.

What do I do? I do have a regular lover and I do sleep around. My lover knows I sleep around, and if we were more serious, I would tell him about all of my hookups. As it is, I just tell him about the extra fun or interesting ones. And if he asked, I'd tell him about the less spectacular ones, too; it's just not normally important to bring up. What is important is that he knows that I have hookups and that a) I'll talk about them sometimes and b) he can ask whatever he wants or needs to know. Meanwhile, he has other lovers, too, and people he's dating more seriously than he's dating me. I know about them and they know about me. In fact, I met him through his longest-term partner, with whom I'm very good friends.

Is your head spinning? Then you've probably never heard the term "polyamory", though that's not a term I particularly care for. Still, if you do a web search on it, you'll find more web pages full of people spouting on about how to do it right or wrong or best or worst than you'll know what to do with. Some of these might be useful. I haven't done such a search recently, so I have no idea what the state of information is at the moment.

Personally, I prefer the term nonmonogamy, and I describe my variant of it as consensual nonmonogamy. I keep people informed, and I expect they'll do the same. Those might be additionally useful search terms for you to consider. I bet they'll lead you to a variety of useful and useless places, but with any luck, you'll find something good.

I'm not going to go into more detail about this stuff, because I find it largely boring to talk about, but before I sign off, I do want to say one thing, and that is that I don't think it's possible to have relationships without someone getting hurt from time to time. More important than pussyfooting or tiptoeing around hoping never to cause pain is being clear and honest and communicating effectively with the people you're involved with. And when pain results, then it's your big chance to be thoughtful and considerate in dealing with it. This is true in any kind of ongoing relationship, whether sexual/romantic, familial or friendly. We can't avoid hurting people close to us, though I hope we avoid doing so on purpose; what we can avoid is being an asshole after we've caused pain. Ignoring or avoiding addressing the unintentional hurts we cause strikes me as vastly more problematic and flawed than causing them in the first place.

Posted by ClueChick at 11:53 PM | Permalink | Comments (3)

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!

Posted by ClueChick at 6:17 PM | Permalink | Comments (7)

I just got my first email from down under, if I read things right! This fellow is newly single after a long time:

So now I am exploring the world of casual loving and am loving going on dates, meeting new people and all the excitement. I've had some great experiences, have come across a problem I've never faced before at the age of 33 - first kisses. Just about all my relationships/shags involved me be seduced rather than the other way around as is usual. Now I have to start making the first move! ... I can sometimes tell when the right time is when the girl is giving me all the well-known body language signs, lots of eye contact and we are generally having a good time. No problem there.

But there are other times, I think when the girl is more reserved that I'm not sure...

So what are some amusing/fun/disarming ways a bloke can go in for the first kiss?

I love this question, and not just because I was fantasizing about kissing on my drive home tonight. Kissing is really great, and it gets short shrift in the world of casual sex; people are often rushing ahead to the main event, missing a lot of great scenery along the way.

I think I'd like to address this question in the course of multiple posts, because there are so many great ways to make a move, and I'd love to hear from readers on both sides of the first kiss (kisser and kissee, if it went down with someone initiating, or kissers both, if it was entirely mutual). What are first kisses that have gone well? What are moves you wouldn't make again if someone paid you? What's a trick that didn't go smoothly but worked out anyway?

But first, let me tell you a first kiss story that has come up several times recently, and that is a very fond memory:

There's this boy. He's super cute, and at the time this story takes place, I'd known him socially for a handful of years, but only peripherally. Around this time, I was getting to know him and his wife better, and we all ended up at a sex party together, where he and I spent some time chatting about a variety of things, including how weird it can be to be at a sex party where it's kind of unclear what your role as an observer is... but that's neither here nor there.

So we're chatting, and partway through the conversation, I was struck absolutely stupid by the desire to kiss him. He was still talking and, apparently, I was, too, though I really don't know what either of us said, because all I could think about was kissing him, and here we were surrounded by people in various states of undress and somehow, I was not in the middle of kissing him, and that was causing me all kinds of consternation.

But, a real problem here is that I'm shy. Oh, sure, I flirt like nobody's business, but when it comes to making a move, I'm about as smooth as a thirteen year old boy. So, of course, I went with the classic route of hoping he'd kiss me. But it wasn't working and thus, we still weren't kissing.

Well, this went on for an embarrassingly long time, until his wife came collect him for bed for the evening. Seeing my moment escaping from me, I decided to leap, and before I tell you what I did, I want to say that in retrospect, I think this is a classy approach that I would recommend to anyone:

We were wrapping up the conversation (I still don't know what we were talking about at that point) and I looked him in the eye and said, "Would you mind if I kissed you?"

He made an eyebrows-raised surprised face and then said, "No, I'd like that!" So we did, and it was awesome. Contrarily, I'm still shy to initiate with him (though, actually, that might add a little bit of fun to our flirtation), but I've had a hell of a lot of fun kissing him from time to time, and I look forward to doing it more in the future.

(Full disclosure: After I told this story to his wife, recently, she then passed it on to him, and he came back to me and said, "But hadn't we kissed the year before at that other party?" And, I'm embarrassed to say he's entirely right, so this isn't actually a first kiss story, but it acts like one, so I'm just adding this addendum onto it, even though it makes me look silly for forgetting the first first time I'd kissed him!)

Posted by ClueChick at 10:16 PM | Permalink | Comments (3)

Last night, I went on about nonmonogamy, but I didn't really talk about the last part of my reader's question: "How have the social constructs of sex and love impacted you, or your partners, if at all?"

To some degree, this entire blog is a response to this question. Social constructs of sex and love are so massively overlapping that it took me a very long time to separate them in my emotional landscape, and I was lucky enough to grow up in a liberated setting where it was never implied that you can only have sex with someone you love. Still, as we all know, there are a lot of social equations that influence how we think and act without realizing it, and our culture certainly has managed to conflate sex and love.

For a long time, it was easier for me to believe that one could feel love for multiple people than that one could lust after more than one person at a time. Now, is that the most ridiculous thing you've ever heard? Come on, there's so much evidence for people desiring multiple others simultaneously, both looking around my immediate environment and looking at media examples, both fictional and non. Where did that idea come from? I blame the ether.

The ideas about sex and love that I find most appealingly countered in nonomongamy center around possession and agency. In a traditional monogamous pairing, partners more or less belong to each other. The degree to which a partnership plays this out varies significantly, of course. For example, my cousin has been dating an incredibly possessive fellow for several years. He gets twitchy when she goes out with male friends, and he insists that if she dresses up and looks hot that she's trying to make him jealous (and, it appears, succeeding.) What she gets out of this clingy form of love, I have no fucking clue, but, then, I obviously prefer a freer version of commitment.

Even when I think I might like to be able to have more say over who my partner spends time with, I'm glad I've chosen a relational style that doesn't allow me to do so, because I don't actually want to be possessive, and this makes me look closely at those urges when I have them. And it also means that I have largely dismantled the idea that love and exclusivity prove each other. I'm sure there are ways to break out of the ownership frame while conducting a healthy monogamous relationship, but since I haven't done that, I don't know what those ways are. Any of y'all who have? Pipe up!

Posted by ClueChick at 8:51 PM | Permalink | Comments (0)

I came across a post or two in the archives where you mentioned the logistics of casual sex in tension with a committed relationship. This caught my eye since I've been dealing with that very issue a lot lately. I've been in a serious relationship with my girlfriend coming up on four years now. I'm nearly 22, and we've moved in together after years of commuting between nearby cities. Recently, we realized that we had never done much of anything, sexually, with other people. Were we missing out on anything? Were there vast secrets of sex which were entirely lost to our naive conceptions? With these considerations in mind, we decided to give one another leave to mess around with other people, because hey, we're open-minded and "hip," right? So that's been working out moderately well, we've explored a bit and learned things and had fun. Trouble is, we both seem to sometimes get the predictable instances of nagging jealousy. I know each of us, when hooking up with another person, is fully aware that it's in no way serious, emotionally - but as a third party to the transaction, it can be difficult conceiving of that hookup occurring, and what it means to one's own lingering competitiveness and possessiveness.

I was wondering whether you had had any similar experiences, perhaps in the early stages of your ... casual sexperiment, as it were. Have you ever run up against these issues, or was it always an easy thing - I'm unattached, sex is fun, I'll go have some? How have the social constructs of sex and love impacted you, or your partners, if at all?

I love this set of questions, but, wow, what a can of worms! Fortunately, I'm not writing for a newspaper, so I can go on as long as I want, or until Law & Order distracts me too much.

First, you won't be surprised to hear that I think it's great that you've decided to check out what else is out there in the world of sexual experiences. A partnership based on affirmative choice is necessarily stronger than the same partnership chosen by default. Not to mention that there is something to be learned, technique-wise, from a variety of partners. For example, I learned to do this thing with my tongue recently that my past lovers will never get to enjoy. But I digress!

I hope, though, that you're not doing this because it's hip. Is nonmonogamy hip? I don't even know. There are plenty of good reasons to play with it, but that's not one of them. But you're a smart guy, so you know that, already.

Jealousy? This is obviously par for the course. As a rule, when I have a regular partner, I don't have any trouble with the partners they have in place when I enter the scene, but I frequently struggle with people who come on board after I do. If I could apply logic to my feelings, I would be able to say that the more clear my partner's commitment to me is, the less insecure I feel when my partner finds someone new. Unfortunately, this isn't the case, so I'm not going to tell you that since you and your girlfriend have a solid relationship and clear communication, this shouldn't be an issue for you. Are there ways to eliminate jealousy? If there are, I haven't found them.

I'm least likely to feel jealousy in very light relationships, obviously. The less invested I am, the less it matters if my lover has other things going, because I don't feel possessive of my time with him or my place in his life. I'm most likely to feel jealousy in a longer-term relationship that wants spicing up that I can't do, because that's something I can't do. I hate things I can't do for someone I love a lot.

Things that help me include talking to my partner and getting reassurance from him that he wants to be with me. That might mean spending extra time together or simply being sure that the time we spend together really "counts" (that is, doing whatever makes me or us feel connected, whether that's sex or reading to each other or working on house projects or walking in the woods or what-have-you.) This can be a good time to check our relationship for lazy spots (Do we spend a lot of our time together both of us IMing with other friends? Are we in a rut that's not taking us anywhere interesting?) and reaffirm our choice in being together. Or it might just be a time to have him hold my hand (or for me to hold his) and say, "Yes, this thing we're choosing to do is hard sometimes."

It may be useful to identify the details of what's happening. Rather than, "I'm jealous when you're out with him," you might examine more closely what's going on. Are you hanging out at home alone while she's out having fun? Do you spend a lot of time mooning over your new lover? What, specifically, gives you pause? I often find that focusing on the little things helps me work through my difficult feelings. After all, I'm not insecure about the big stuff, so even though jealousy feels big, it's often simply a reaction to small things.

There are a lot of things I love about being nonmonogamous, and I could go on and on about it, but far be it from me to suggest that it's the right thing for everyone, and jealousy is one of those things that just about everyone runs up against. That doesn't mean you're doing anything wrong, and the main thing I can suggest for dealing with it is to communicate clearly about what's happening.

Tomorrow, I'll talk about sex and love and how that relates to nonmonogamy for me.

Posted by ClueChick at 10:59 PM | Permalink | Comments (0)

Well, then! I will certainly give someone a blowjob in celebration of the hopeful turn of yesterday's election. But first, I need to have some anal sex to mark my specific celebration with regards to Mr. Santorum of PA. (For those of you who don't understand the link, click here.

But I now return to my regular night job of dispensing opinions, advice and all-out snarking:

While in a local bar the other night I found myself flirting with my waitress. She seemed to welcome it - lingering at my table, holding conversation beyond "what do you want to drink next", etc. What suprised me was that she actually made physical contact with me - touched my shoulder when asking if I needed another beer, and leaned up against me lightly to point me in the direction of the bathrooms.

So I have two questions: one, was this a sign that I should have left her my phone number (I didn't, though I left a nice tip), and two, is trying to pick up your waitress extra-gauche?

I'll start by saying I've never waited tables, so I could totally blow this one. I encourage any women who have direct experience here to weigh in.

But! Yes, you should have left her your phone number. If you ask me (and you did), it's never gauche to pick up a woman who's clearly flirting with you. (Okay, that's not true if it's, say, your best friend's fiance the night before the wedding and she's really drunk and they haven't talked about it first, but let's consider most reasonable examples, here, shall we?) As long as you, personally, are not skeevy (and if you are, she's probably not flirting with you), you're in good shape. Also, leaving your phone number is extremely low-key as come-ons go.

In fact, my first thought here is that, well, of course you should leave your number! But because women are often used to being the pursued rather than taking the initiative, if you actually want something to happen, you might do better to ask for her number. But, really, if she's flirting that much, she ought to be able to pick up the damn phone herself, right?

So, now I have an assignment for you: go back to the bar, flirt with her, leave your number, and report back, 'k?

Posted by ClueChick at 6:24 PM | Permalink | Comments (2)

Today, I address a question from a reader, which I got ages ago and just rediscovered:

Should a guy just listen, or try to solve the his girl's problems?

My friends joke about "male answer syndrome," which is what happens when they talk to their boyfriends about a problem and the boyfriend immediately starts offering solutions, even if they're just looking to vent.

I've seen this pattern repeat itself irrespective of gender, though, so let's broaden out the question a bit. This isn't just a matter of how a guy should be with his girlfriend's problems, but how people, in general, can be helpful to each other.

First, if you have a problem, you can help yourself by being clear on whether you're looking for sympathy or suggestions. I'm often looking for sympathy and rarely for suggestions, personally, and I can save myself the aggravation of unwanted advice if I start the conversation with, "I just need to vent." That way, I figure I'm perfectly justified in biting the head off the imprudent person who tries to tell me what to do!

But many people don't do that. So, say you have a lover who's talking about an issue. What should you do? I suggest a clarifying question: "Are you looking for ideas or advice, or just a listening ear?" That's really the only way to know what the right approach is. Save this question for later, too, because the answer will be different in future conversations, as well.

Sadly, there is no one-size-fits-all answer. If only life were so easy. Of course, then I'd be complaining about it being dull.

Posted by ClueChick at 10:01 PM | Permalink | Comments (0)

I recently received this query:

Why is sex so important in your life? I mean I of course understand people want to have fun and I'm not at all against it, but I think smoking pot while listening to good music, or drinking half a bottle of tequila while listening to rock music, or jacking off while looking at pictures and videos of your favourite kind of perversion on the internet is a lot better than usual sex, because, in these cases, you don't have to adapt to the wishes of somebody else and make him/her adapt to yours, but you can just do everything as you like. So, why?

I'm having a "same planet, different worlds" problem trying to think about how to answer this question. Maybe it's because I've never smoked pot? I have drunk half a bottle of tequila, though, and I like sex more, so maybe it's just a different experience of the same sorts of things.

It's true that playing by myself is pretty great, and it means I can do whatever I want to myself, within my abilities, and I would never, ever give up masturbation, but neither would I give up partner sex. In some ways, these two things are so different that it wouldn't even occur to me to compare them. It's like the difference between hanging out at home with a video vs. going to a party. I'm unlikely to do both in the same evening, but my life just wouldn't be complete without a bit of each, and some other stuff, too.

But, then, I've been accused of being a bit of a variety junky.

Still, why is sex important to me? For some of the very reasons that you seem to think it sucks: I like adaptingg to someone else's desires, and I like having others adapt to my desires. Having sex with someone else brings a totally different kind of energy into the bedroom (or living room, or kitchen, or...) [Note to roommates: Don't worry, I put a towel down on the couch, first.] Getting myself off is completely different from fucking, or sucking cock, and no matter how good I am with my fingers, having someone eat me out is a whole different thing, too. No matter how much I try, I can't give myself the same electric buzz of a lover's hand stroking down my back, and I don't care what kind of attachments they're selling for vibrators these days; there's nothing like having my lover fuck me from behind.

Even setting aside all of that, sex is great because it's an opportunity to connect with someone outside of myself. It's not a very popular attitude to have these days, but I really like people. I like the differences between them, and the similarities. I learn new things with every new person I meet, and the things I learn from new lovers are some of my favorites. I feel powerful when I'm having sex, and I feel vulnerable, exhilarated, protective and protected. I get a huge rush from sex with other people that is completely unlike the release I get from jilling off to porn on the internet.

I would no more trade sex for masturbation or alcohol (or vice versa) than I would trade people for books. For me, these are entirely orthogonal drives and desires.

Posted by ClueChick at 5:16 PM | Permalink | Comments (4)

I posted last month about the joys of the out of town hookup, and I received a couple of questions about that sort of arrangement.

First, how do I protect my valuables?

This, of course, is an issue at home, too, and I'll admit that I'm actually pretty lax about this. I don't tend to think of guys who are looking for casual sex as big into thievery, but, on the other hand, you never know, right? At home, I make sure that my valuables aren't sitting out in plain sight. I actually have to admit that my room is a little on the messy side, and I think that probably makes it harder for someone who might otherwise be inclined to take advantage of something sitting in plain sight to do so. Also, I rarely leave a guy alone anywhere in my house for more time than it takes me to run to the bathroom, and I wouldn't unless I knew him well enough to have an ongoing arrangement with him.

In a hotel, I'm probably better off, since most of the hotels where I stay have safes, and that's where I put my wallet and anything else valuable I might be carrying with me on that trip. I suppose a guy might run off with my business clothes, but it would be hard for me to get too upset about that!

The second question was how do I decide where to meet people when it's not my "home turf"?

It's true that when I'm at home, I know the neighborhoods and I know where I'll be safe at the time of day I'm meeting my potential hookup. I also know the cafes and bars that I like to visit, whereas, when I'm out of town, I'm going on someone else's say-so. As a rule, I like to use my hotel's bar or lounge, if it has one. This has two advantages: I don't have to venture out on the town in an unknown neighborhood, and if I like the guy, we can easily go up to my room.

There have been two times when this plan wouldn't work. Once, I was in a hotel with no lounge, and the other time, there was a very nice lounge, where many of my company's clients were enjoying an after-dinner drink. In both of these cases, I'm afraid I just lazy-ed out of the hookup. In the case of the hotel with no lounge, I'd already been in contact with a couple of potential guys before going to the hotel. Once I got there and saw that I'd have to find another option (and that my hotel was in an uninteresting business area), I decided I was more interested in watching reruns of Law & Order than trying to manage logistics, so I emailed my guys to say it wasn't going to work. In the case of the hotel with lots of clients, I knew that was going to be the case, and I simply chose not to make any hookup arrangements.

The truth is, I'm lazy, so if a hookup is going to be too much work, I'm unlikely to bother with it, especially for an out-of-towner.

Posted by ClueChick at 7:33 PM | Permalink | Comments (1)

One of my loyal readers wrote me this morning to ask,

I had an interesting first meeting w/a potential hookup recently that brought up a question for you. We were ogling each other over drinks and the topic of clothing choice for a hookup date came up.

Specifically, the question of how much skin to show. She preferred tight shirts that showed the definition of pecks (for men) and breasts (for herself). I tend to go with a button-up shirt that shows a little neck and like seeing ample cleavage on a woman (not that she necessarily needs to be well-endowed, even cleavage on small women works for me).

What are your preferences, for yourself and the men you "see"?

This is funny timing because just last night one of my lovers and I were talking about clothing and what's sexy. Some friends bought me a custom corset for my birthday, and almost everyone I know thinks I look particularly good in corsets, but he was saying that corsets leave him cold. Go figure.

The thing about clothing is that there are, as usual, several things happening. First, you obviously want to wear something that feels good, comfortable, flattering. And you want to wear something that's going to attract your (potential) lover. When your date is someone you don't know, though, you don't know what will be attractive to them! So, what to do? Fall back on what's attractive to you, of course.

This makes sense, and I think it's a good approach. Alternately, there's always the choice of wearing an outfit that nets lots of compliments.

Personally, I like to wear an outfit that looks good (to me), but, more importantly, that feels sexy. I'm pretty sure that when I feel sexy, I project sexy, and that's a good thing to do on a first date (and even better on a second date!) So, what am I likely to wear? In the summer, which is, I must say, way better for flirty attire, I'm fond of flippy skirts and a lacy camisole. This ends up showing a fair amount of skin and being rather clingy, at least on top. I also have a couple of fun little dresses that I like. And, depending on how I want/expect the date to go, I may or may not wear panties. But that might be another post.

As for my dates, I'm not sure I care a whole lot about what they wear. For a first date, I like to get the impression that he's put a little effort into his attire, but it's far from a deal-breaker if he hasn't. I mock men whose pants fall off their hips at the slightest provocation, but I like it when I find that my date's pants needs only the most gentle encouragement once we're in the bedroom. I love touchable fabrics, as they give me an excuse to put my hands on him. And I really like my date to look comfortable in whatever he's wearing. That sexy thong isn't doing you any good if you spend the whole evening squirming as a result of wearing it, after all.

Posted by ClueChick at 7:59 PM | Permalink | Comments (0)

One of my readers recently emailed me with this query: "Have you ever had an internet sex experience using a webcam or otherwise? What do you think about them?"

I'll answer the easy part first: I'm a technological stick-in-the-mud, so I don't have a webcam. My laptop is 5 years old, and I think it would die a horrible death if I tried to make it do more than the basic web-browsing, music-listening and blogging that I currently do with it. I have watched other people's web cams, but since I'm not all that interested in watching guys jerk off if I don't even have the chance of (ahem) hands-on participation, it's a lot less interesting to me than it seems to be for the guys who like the chance to be an exhibitionist.

So, yes, I've had a sex experience using a webcam, if you count me having the webcam window running in the background while a guy jerked off, but it didn't do anything for me, so it didn't feel sexual to me.

As for what I think about webcams... well, I've had some fun with sapiophile's, but usually when she and I are getting frisky and teasing another friend of ours, but that's mostly interesting because we all already know each other and are just playing around. It's not, for me, particularly hot. But I certainly know women who enjoy it a lot.

For me, I'd rather be doing it in person, or playing more with my imagination, which means either phone sex, or the much maligned "cyber". The benefits of playing face-to-face are so obvious that I won't go into them. But why would I prefer phone or cyber sex to webcamming? Well, what if I'm feeling cranky and out-of-sorts and don't feel like putting on a show? Or what if I want to think about doing something that's too logistically complicated to actually act out? Or what if I want to ... well, pretty much everything I'm looking for in a sexual exchange that's not in person involves my imagination, which works best if it's not distracted by having to watch someone or think about how I look while I jill off. Or, um, whatever.

So, no, I don't have much interest in webcams, but I'd actually be interested to hear from folks who like them a lot, because maybe I'm just missing something because of lack of experience or exposure.

Posted by ClueChick at 4:45 PM | Permalink | Comments (3)

This morning, I received a query on a topic that's often on my mind:

Dear ClueChick,

I've run into an interesting issue of late and I'd love your thoughts. The last two women I've met for casual encounters had the interesting issue of being unable to have an orgasm when having sex with a stranger (i.e., me). They assured me it wasn't my performance that caused the lack of orgasm, just a general issue with all new guys they sleep with. Despite this, they continue to have and enjoy casual encounters.

How important is the orgasm to the casual encounter? Do you experience one the first time you're rolling around with someone new?

Now, I could go on and on in my response, here, but I'll try not to bore you all too much. First, of course, each person places a different level of importance on the orgasm as part of the sexual experience, whether casual or otherwise. I happen not to place a lot of importance on it, because I almost never get off when I'm with a partner, casual or committed, but I still enjoy sex quite a lot (obviously). For someone for whom orgasm is less of a hurdle, I suspect that the big O plays a more important role in the whole experience.

So, no, I don't come the first time I'm fucking a new person, and probably not the next several times, either, because it takes me a while to get comfortable enough with someone to be able to talk about the details of my complicated relationship to orgasm. To say it's a loaded topic would be both an intentional pun and an understatement. I've never wanted to turn my sexual experiences into a possibly-fruitless quest for an orgasm when I enjoy the whole shebang uncomplicatedly without.

That said, I always like it when I'm with a lover who cares about my pleasure. This can be a tricky topic, itself, because, of course, I like my lovers to give me the opening to say what I need, but I don't want them to be pushy about it if I say I'm not going to come. On the other hand, I imagine it must be frustrating for them. I imagine how I would feel if my lover never came, and I'll tell you, it would definitely make me doubt my mad skills in bed, so I've decided to go on a quest to get off with partners more often. The trick there, of course, is to find partners with whom I can explore this topic, touchy bits and all. Needless to say, this is not casual encounter fodder. That's another post, though.

All that said, I assure you that sex can be a hell of a lot of fun, even if there's no orgasm, and as long as you're giving your lovers a chance to tell you what would help them get off and are showing that you're interested in making that happen for them, you're doing what you can. Reaching orgasm in any encounter is a two-person interaction, and if your lovers say they just don't get there the first time(s) with someone new, they ought to know. With any luck, you'll get a chance to test the theory that it's just the getting-to-know-you factor.

Posted by ClueChick at 5:09 PM | Permalink | Comments (0)

One of my female readers asks, "The men that have contacted me I'm not interested in. Am I obligated to respond or is it better to just ignore them?"

Ahh, the ongoing question of how to deal with men you're not interested in. This is always a struggle. On the one hand, you don't want to be a jerk and ignore them, but on the other hand, it's awkward to decline them, and ignoring them is less blatant and rude online.

I will admit that I often feel like I'm being rude when I don't respond to someone's approach in response to one of my ads or profiles, but that doesn't stop me from doing it, and I think that's okay (obviously). On those occasions when I've responded to say, "Thanks, but no, thanks," about a quarter of the time I don't hear back, a quarter of the time I get an appreciative response, and half the time I get the guy badgering me to give him a chance. Sometimes it feels worth it to me, and other times not, to take the trouble to respond, but I never feel obligated, and you shouldn't, either.

On the other hand, if a guy has obviously taken a lot of time to write a thoughtful and interesting email, I'm often pleased to be able to say, "Hey, I appreciate the effort you put into your email," even if I don't find him appealing. And, unsurprisingly, the guys who write the good emails are more likely to be the ones who respond positively when I decline.

Posted by ClueChick at 5:59 PM | Permalink | Comments (5)

A readers asks, "How much emotion should a guy show?"

As always, with this kind of question, I'd like to begin with the caveat that the answer depends on at least three factors: the guy, the person he's dating/fucking/whatevering, and their relationship.

First, the guy: How much emotion is it natural for you to show? I don't really buy the line that men are naturally less emotional than women, though I do see that men are given fewer socially-approved opportunities to show their emotions. I, for example, play my emotions relatively close to my chest. This means that when I'm in a new relationship, the person I'm seeing is unlikely to get to see a whole lot of what's happening under the surface. Furthermore, there are layers of what's happening. If I'm having a good time on a date, I can be happy and smiling and laughing, or I can choose to open up more and talk about how much I enjoy spending time with my date, or open up further still and talk about what I think that might mean for the future of our relationship. All of these are choices about how much emotion and/or internal life to share with a date. Only you know what's comfortable for you.

Second, the person you're dating: I've been on dates with guys who tell me too much too soon, and it's not pretty. I don't want to know about your depression support group on our first date, and I don't want to know that you feel so comfortable with me that you can tell me about your embarrassing thumb-sucking habit over coffee. I do like it when people are comfortable with me, but until I know you better, I don't have enough texture to my sense of you to be able to respond reasonably to early oversharing. This makes me feel awkward, and I hate feeling awkward. On the flip side, if we've been dating for a while and we're still having only superficial conversations about the weather, I'm going to think you're one of "those" guys who never makes room for a real connection, and I'm likely to write you off.

Third, the relationship: Are you casual fuckbuddies? In that case, even after a few months, your relationship isn't going to have the structure to allow for conversations that bare the soul. Just because I've sucked you off doesn't mean I want to hear about how your parents were never at your elementary school plays and how much that hurt you. On the other hand, if you have a relationship that's heading for more significant intimacy, whether friendly or romantic, it'll be weird for you to keep your partner at arm's length and never talk about the things that are on your mind, whether good or bad, whether related to your relationship or simply the day-to-day workings of your life.

Finally, the balance of what to share, in terms of your inner life, with a friend or a lover, is one that many people make unconsciously, and that often works well. Conscious awareness of some of the factors that play into this never hurts, though, right? In general, people take turns opening up and seeing how the other person responds. If I share more about myself and the person I'm talking to doesn't get all weird about it, and then, in turn, opens himself as the conversation continues, we can continue to deepen the intimacy/personal-ness of the conversation until someone takes a step that the other person isn't willing to match. Then you stop there, and either try again to deepen the intimacy at a later date, or the relationship stays at that level. (To be clear: staying at a given level, as long as both people are happy/content there, is a great thing.) Over time, friendships and romantic relationships shift around, sometimes being more and sometimes less intimate. In new relationships, however, you're still working out where your baseline level of shared comfort is. It's up to you, when your partner makes an intimacy-overture, whether you want to meet her or not. And pay attention to whether she meets yours.

Finally, beware of rushing into intimacy before your relationship has the structures to back it up. My one blazingly bad idea of a fling was a case of both of us diving head first into the emotional intensity of the potential of our connection without checking whether our lives could actually fit the shape of the thing together. In the end, we couldn't, and the dramatic backlash of that has fucked up the potential for some steamingly hot sex ever since.

Posted by ClueChick at 10:28 PM | Permalink | Comments (0)

A while back, I asked people to ask me things they'd be curious to know about, and Lil wrote wondering about deal breakers in serious and casual relationships. I'll start with talking about deal breakers even before I get to the relationship stage.

There are a few:

I won't fuck guys who are cheating on someone in order to fuck me. It makes me feel yucky and I don't like it. (Yucky is obviously very different from naughty, which is hot.)

I don't do guys who smoke (cigarettes).

I won't even talk about sex with a guy who gives me a hard time about condom use.

It won't get as far as talking about condoms if a guy can't write coherently and in a way that doesn't make me feel like he thinks I'm an object for his pleasure and convenience rather than a person with wants, opinions and interests of my own.

No doubt I could come up with some others, but those are the bare bones ones that leap to mind when I think about the hurdles a guy has to pass before I'll take him seriously as a prospect.

Posted by ClueChick at 10:43 PM | Permalink | Comments (3)

While I was away, B asked, in response to styles of casual sex, whether I have a preference of what style of casual sex to have.

I do, in fact.

I find one night stands tiresome. Because I expect some email exchange before arranging to meet someone, and then a non-sex meet-up first, before even getting around to the fun part, one-offs are a lot of work for not much payoff. Also, although I know some people really get off on the first time with someone new, I find that I have more fun in subsequent encounters. As I get to know a lover better, I relax more, and we become more comfortable with each other, not to mention moving into fun fantasy territory.

I enjoy the light, ongoing thing, where whenever we're both available and horny, we can make plans and have some fun. This is the epitome of no strings attached, for me, because it's very fluid, but by getting together regularly, a light relationship does form, which provides a platform for more adventurous exploration.

These days, however, my favorite is the friends with benefits style arrangement. Here, the sex may be casual but the relationship isn't, and depending on how you set things up, you may arrange playdates ahead of time, or just play it by ear like with the looser arrangement I described above. Mainly what I like about this is the opportunity to plan ahead, which, since my life is pretty full, helps me be sure to make time for sex (I know, it's kind of sad that I have to plan ahead for it, right?) in any given week.

In fact, recently, my sex drive is high enough that I'm considering actually picking up a regular old boyfriend so I can plan on having sex on an even more regular and frequent basis. But that's a whole different post :)

What about you all, readers? Do you have favorite formats of casual (or otherwise) sex?

Posted by ClueChick at 7:17 PM | Permalink | Comments (4)

In response to sapiophile's well thought-out post on picking up hot fat chicks, DJ commented, "Hi ClueChick. Why not post a pic on here so we can see how beautiful you really are?"

I don't post a pic for several reasons:

First, I like to be anonymous. I don't need my parents surfing their way here and finding a big picture of me attached to a long story about how I fucked that hot guy I met on the internet. Furthermore, I don't need my future employers doing a web search on me and finding the same. And that's not even getting into the messy can of worms I'd prefer to avoid with people who know me in real life thinking that just because I write a blog about casual sex means that I'd love to fuck them casually and whenever they like. A funny little secret about me is that I'm actually quite picky and (don't tell anyone) kinda shy.

Second, I already get lots of offers from my readers to let them take me out for drinks or the like. I didn't set up this blog as a way to meet people, and I think a picture would confuse things.

And third, people could look at my picture and do one of two things: Either they'll see how gorgeous I am and decide they have to get in my pants, thereby ignoring my advice. Or they'll see how totally not gorgeous I am (hey, everyone's taste is different, right?) and decide that all my advice is sour grapes and thus not worth listening to.

My point in writing this blog is not to set myself up as some fabulous sex symbol, but just to be the voice of everywoman, or at least every-woman-who's-enjoying-casual-sex, and toss out some of my observations and advice in hopes of a) helping clueful men get laid and b) helping women who like casual sex have better options among the men.

As I've suggested in the past, if it would help you to picture what I look like, you should feel free to think of some woman you think is extraordinarily hot and imagine her writing this blog. Just for kicks, of course. Alternately, you can think of me as a fairly average woman: hotter than some, less hot than others, but who happens to write reasonably well, which is why you keep coming back to read my blog, right?

Posted by ClueChick at 8:34 AM | Permalink | Comments (1)

Sapiophile asks, "Does exchanging keys and reserving a drawer in one another's domiciles always mean it isn't casual anymore?"

Yes.

I'm tempted to leave it at that, but that's not much of a post, now, is it?

Casual relationships can take any number of forms, some of them more regular than others. In fact, though none of my casual relationships have involved trading more than phone numbers and saliva, I can imagine an ongoing-but-casual thing that would result in trading keys. In fact, that could facilitate the playing out of all kinds of fantasies, but that's another post.

But the point at which you're making room for each others' stuff in your homes, it's no longer casual. Sorry.

Posted by ClueChick at 7:59 AM | Permalink | Comments (1)

In a comment on yesterday's post, wotw asked,

This problem comes up repeatedly. It's a first date. We hardly know each other. She asks: "So what do you do for fun?". The honest answer is: "Stick weird foreign objects up women, set people on fire, host (with invaluable help from invaluable friends) large get-togethers for sexually open people, etc."

I do usually get around to telling them about this stuff, usually on about, oh, the second or third date or so. But the first five minutes of the first date seems a little soon.

On the one hand, this stuff takes up a lot of my time, and crowds out a lot of other things I might do for fun---so if I don't mention this, I'm sort of at a loss for an answer. I end up saying someting really stupid like "Oh, you know, I like all kinds of stuff."

Or I say something like "I read a lot", which is moderately accurate (actually, "I buy a lot of books" is more accurate), at least as a matter of fact, but grossly inaccurate, I think, as far as conveying information about my funloving nature.

Help me, Cluechick! How do I answer this question?

This is a great question. There are lots of kinky people online, as we all know, but there are also lots of people who aren't kinky. And there's a time that it's reasonable to talk about your kinks and darker desires, but the first few minutes of conversation are rarely that time.

So, I recommend that you lie.

Okay, wait, no, sorry, I didn't mean that. But it doesn't hurt to have a few innocuous things that you can talk about in those first minutes before you get into some of the more, ah, extreme interests. While I'm a strong proponent of honesty in general, I'm also in favor of the occasional white lie to help people save face or to keep a new social situation flowing smoothly. This is probably one of those times.

Your approach of talking about books is a good one. Other fairly innocuous topics might be movies or current events (though that gets dangerously close to politics, which might also be best avoided), travel, or what have you. Now, innocuous topics will not, in fact, help immensely in conveying your fun-loving nature, as you put it, but they will help to break the ice, let you and your date get comfortable with each other, and come to feel comfortable enough that you can broach the topic of the last weird object you inserted in a woman. (That reminds me of a fellow I fondly called Insertibles Guy, but that's another story.)

Remember, in the first few minutes of talking to someone, you're not necessarily trying to convey every last tidbit of information about yourself, but rather, are just getting started on striking up a rapport.

There is, of course, another hand to this answer, however: If you would not be interested in dating/playing with/fucking this woman if she's not into the sorts of things that you're into, then you have very little to lose in scaring her away early. If she's into the sort of play that you are, she's probably not going to be nonplussed by your opening the conversation in that vein. I, for example, have been known to enjoy a variety of activities that might not be found on the regular menu, and I'm generally pleased when someone I'm flirting with lays out his interests early so we can see what overlap we have.

On the other other hand, you never know what she might be interested in trying after getting to know you and how fabulously attracted she is to you.

All of this is to say, then, that you have two basic options, both reasonable: Start on innocuous topics (which you will probably want to think about ahead of time), or dive right in. I recommend that you use your judgement on which to use based on the balance between how disappointed you will be if you don't get to stick weird objects in her because you've scared her away and how disappointed you will be if you get invested and then find out you won't get to stick weird objects in her.

Posted by ClueChick at 6:38 PM | Permalink | Comments (0)

The other day I posted wondering what questions you all might have, or topics you'd like to see me post on. I had a few responses, all interesting. Today, I'll address b4f's question:

How much casual sex do you think is actually going on out there? Is it a select few folks like us who choose to spend their nights pawing and sniffing each other or is the world essentially one giant pick-up bar with a few prudish naysayers on the sidelines?

The truth is, I don't have any good idea about this, because I spend almost all of my time safely ensconced in the cozy and, yes, sexually free environs of my home and neighborhood. Here, even those people who aren't engaging in casual sex either have in the past, or take a rather laissez faire attitude toward it, which makes it seem normal to me. I understand that in vast swaths of the country, and even in other social circles in my very city, this isn't the case.

So, although I may perceive that there are lots of people running out and having as much casual fun as their hearts may desire, I think the truth is that we're probably a rather select few.

Looking at Craig's List for a bit of insight here, there are many hundreds of posts each from people in my city alone. And they're all looking for casual sex. Now, sure, there's a lot of repetition, but you also have to assume that not everyone is looking there. And then, of course, there's the bar scene.

So, I think there's a lot of casual sex happening. Probably most of it is happening in younger crowds; I'm 30, and by this time, most people are settled or settling down. And probably most of it is happening as a filler, rather than as a life-oriented practice. But not all of it! I know there are plenty of people of all ages who enjoy casual encounters and have no desire to change that. I just don't have any idea how many there are!

I do, though, think that we are the few... the proud... the, um... well, I don't know what our title is, but we're out there!

Posted by ClueChick at 10:56 AM | Permalink | Comments (0)

Dear CC, Why does casual sex make me insecure? Signed, Hot But Insecure:

Dear Hot But Insecure:
First, casual sex IS less secure that committed sex. After all, sex in a r'ship has a structure and clear expectations and boundaries. When you're dating someone, there's a generally accepted path and unspoken rules that most people follow. Casual sex, on the other hand, is fluid and doesn't have much in the way of rules. So, while, when dating, you can reasonably expect your lover to maintain regular contact, be it a phone call the next morning or an email touching base midweek, in the casual sex setting, you can reasonably expect your lover to either call you in the morning or not, to let you know what he's doing later that week, or not, etc. That's unsettling, and it leaves the niggling gremlins of your imagination to go to work.

And what do those niggling gremlins focus on? The natural insecurities that everyone has, of course. In this case, they probably make you think things like, "He hasn't returned my email in 12 hours. That must mean he never wants to talk to me again! And the reason he never wants to talk to me again is that I'm unattractive and boring and I give horrible head! This means I'm a bad person, and I'll never find anyone to date, or even fuck, ever again!

Pay no attention to the gremlins in the corner. The insecurity is normal, and if it drives you to distraction, you may decide casual sex isn't for you. Or it may mean that in your casual engagements, you need to set up systems or understandings that clarify the process for you and help you avoid those insecurities. And, of course, doing what you can to allay your own fears is important. Remember, you're awesome. Make a totally immodest list of all the awesome things about you. Ask your friends to help. I don't know if that'll help with the insecurity, but it sounds like a fun project, doesn't it?

Best, CC

Posted by ClueChick at 11:19 PM | Permalink | Comments (0)

Yesterday, I got an email, perhaps inspired by Sunday's post asking, "What's the weirdest thing one of your people has asked you to do?"

Before I answer this question, I want to make a general statement:

People, be careful what you ask me, because I'm basically an open book, here, and some of you aren't going to like what you read.

So you should only keep reading if you're really sure you want to know the weirdest thing (by my lights) that a lover has asked me to do since the commencement of my little fling with casual sex.

Okay, you're still reading, so I'll tell you: About six months ago, there was a guy who presented as basically normal, and who was generally fun in bed, when we got to that. But he really took me by surprise when, mid-fuck, he asked me to spit in his mouth. I mean, I know people get off on all kinds of things, and intellectually, I get the appeal of the spitting thing, but in practice? It's not so much my thing. Of course, as the spitter, it's pretty low-impact; it would've been different if he'd wanted me to be the spittee. Needless to say, though I found his request weird, it was also easy to accommodate.

I'm sure some of the other things I've been asked to do would rate higher on some people's weird scales, but that one definitely took the cake for me.

Posted by ClueChick at 10:20 PM | Permalink | Comments (1)

The other day, this query appeared in my inbox:

How cuddly should a guy be?

I have to tell you, I don't really know how to answer this kind of question, because the answer depends so much on the individual you're with. Really, the best way to find out how cuddly you should be is to ask your partner. Or act as cuddly as you like, and if she finds it excessive, she'll probably take some of her space back. Or if it's not enough, you'll find her touching you more.

Speaking for myself, I tend to be a little less on the cuddly side than many. I like to touch, but I don't like to be entwined or tangled for more than a few minutes. I like spooning, but I far prefer to be on the outside 99% of the time. I love friendly touch: stroking his arm or back or standing close enough that our shoulders touch. I also like to receive that kind of touch.

So, now you know what to do if you ever get me into bed. But, really, if you're sleeping with someone else (which I assume you are, since you're not sleeping with me), I suggest you ask her what she likes!

Posted by ClueChick at 10:24 PM | Permalink | Comments (3)

I'm a bi poly woman who likes to have casual things with strangers a couple of times a year. My steadies are fine with this, and I always follow the rules, like condoms and stuff. But I'm never sure should I tell the people I'm picking up about my other partners, or does it even matter?

I love this question., in part because I'm really not sure about the answer! But I'll take a stab at it, anyway.

The good news is that I think you're in the right either way. Barring objections from your partners, you can tell your fuckbuddies whatever you like: You're following the rules you've agreed upon, and it may or may not be relevant to share that those are rules you have with another person. After all, you may be using condoms in part because you've agreed with your partners to do so, but I certainly hope you'd be using them even if you were otherwise single!

An advantage to telling your flings about your other partners is that if you have rules that are more strict or unusual than "the norm" (whatever that is), it's an easy excuse/reason. "Why do you have to use latex gloves to touch my dick?" says he. You can say, "My boyfriend's only okay with it if I use gloves. You choose." I can't imagine a guy on CL who'd turn down a gloved hand in favor of no hand.

A disadvantage to telling, though, is that you may then find yourself explaining that, no, it really is okay with your boyfriend, and, yes, that's how you do things, etc. Some people love to talk about their relationship structures, and others find it tiresome. That's totally up to you.

Obviously, the main drawback to not mentioning it is that if your fling turns into something more serious, you have to find the time to bring it up, and, personally, I think there's no good time after fucking to say, "Oh, by the way, I have this person I've been seeing for a few years..."

I'd be curious to hear what other nonmonogamous readers do on this one.

Posted by ClueChick at 4:05 PM | Permalink | Comments (3)

My post on race generated a flurry of responses, in comments and in my inbox, and I'd like to address the primary question that a couple of people asked me: Why do I think I haven't dated a black guy?

I suspect I'm not the best person to answer this question, but I'm not going to call my therapist for her insight, so you'll have to make do with my self-analysis. I have, of course, received responses from black men to various posts on CL, and to a couple of my profiles on dating sites, and there have been some instances where I was interested enough to email back, and, a handful of times, to meet up, but it's never gone beyond the coffee date. Why not?

First, and possibly most impossibly lame: I feel a certain amount of embarrassment about my theoretical interest in black guys, and this makes me distrust my evaluation of the attractiveness of any particular black guy I meet, because, gosh, is he actually hot, or am I just in love with the idea of fucking a black guy? I mean, I think about it, and I imagine how my pale hand would look touching his dark shoulder, or my tongue on his nipple, or my mouth on his... well, you get the idea. I'm not comfortable being hot for an idea and projecting that onto an actual person, even if the person in question wouldn't actually mind, and, needless to say, I've never actually brought it up in a conversation with one of my potentials (though a reasonable argument could be made that I ought to!)

Second, I know I'm racist. (And you are, too. If you think you can be free of racism in this society, you're fooling yourself.) And I worry about how that might play out in a relationship, even a light one, with a black man! When I spend time with a black guy in a setting with a lot of potential, I feel shy, that I might say the wrong thing (more than usual; despite the blog, I'm not actually all that smooth) or do something silly, or just generally prove what everyone already knows: I'm a white girl who mostly hangs out with white folks.

I'd like to get over these hangups, and I like to think that I will, eventually, but I hate to think about dragging some poor guy along with me for the ride. And that's the main reason I've yet to date or fuck a black guy.

Posted by ClueChick at 5:34 PM | Permalink | Comments (1)

On Monday, I wrote about couples looking for men for threesomes, and in response, I received this query:

What if i'm a guy and I want to find another guy and a girl to hook up with? What's the best way to find other people who are into this?

Well, first off, you probably won't have trouble finding a man, because, well, as I've previously remarked, there are lots of men out there looking to play. The trick, with regards to picking up men for your purposes, may be in finding a guy who wants to play with men and women. Straight guys don't want to get in bed with boys, and gay dudes shudder at the thought of getting naked with a girl. So, you have to find that rare type: the bisexual. Or the heteroflexible, which may be more likely. Or the gay boy who isn't skeeved by tits. In general, I find that people have a hard time with that gray area in the middle, and especially men are caught in this bind.

(Side note: if you think that only women are hurt by "the patriarchy", think long and hard about just how inflexible and limiting images of male sexuality are in popular culture. If liberation means that we all get to live in ways that honestly reflect our inner selves and desires, then it's clear that men have a long road ahead of them before they're able to break free of rigid images of the manly man ideal.)

As for finding a woman, of course, you know this is going to be a challenge. Because women are fewer and farther between in the casual scene to begin with, and then, on top of that, you're looking for a woman who's open to something that's slightly off the norm. But I'll tell you a cheery little secret: lots of women fantasize about getting with two guys. And lots of the women who are already inclined to go looking for casual encounters are probably the types who are sexually open enough that they're the sort who just might be interested in some hot boy on boy on girl (or boy on girl on boy, or girl on boy on boy, or... well, you get the idea) action. So, in fact, simply by looking for this sort of thing, you're setting a "hook" in your ad that is likely to help you in your search.

I would recommend that you try posting several variations of your ad. You may find that this works best in a couple of steps: first meet one, then together look for the third. Or, you may find that you meet up with people who like the idea of getting with a totally new combination of people. You never know. But, oddly, I'm more optimistic about your chances than those of a regular guy looking for a straight-up boy-girl thing. I definitely want to hear back from you on how it goes!

Posted by ClueChick at 8:35 PM | Permalink | Comments (0)

I know this is a little off topic for you, but I'm married, my wife and I like to have threesomes, but mostly with other men. I'm bi, but our guys don't have to be... whatever works is good! Even though there are lots of men looking for hookups out there, we sometimes have trouble finding the real deal. Any tips?

Gosh, I have to admit, there's part of me that's shocked to hear that you're having trouble picking up men. I mean, sure, as a couple picking up men, you're limiting your field a bit in comparison to say, my field, which is pretty wide open, but even so, there are an awful lot of men out there, many of whom are open to somewhat, ah, unusual experiences and encounters.

That said, on the other hand, a lot of guys are pretty freaked out at the idea of getting naked with another man, even if there's no suggestion that there might be contact between them. Because of the all-or-nothing view of homosexuality, especially male homosexuality, even a whiff of comfort with other men in a sexual context can strike fear into the hearts of many. Lame? Absolutely. But real? Yes, that, too.

I suggest that you alternate between mentioning your bisexuality and not mentioning it, in different ads. In my experience, picking up men for MMW play, those men who are interested in a bisexual sort of encounter will mention it on their own, even if they've never done anything like that before. If not, then on those occasions that you don't raise bisexual play as a possibility, you shouldn't mention it, either. If, in fact, you're happy with either type of encounter, you can cast a wider net by not pushing that fear button.

On the other hand, part of me wonders how much fun it really would be to have an encounter with someone who might flip out to know the rest of the story. Sometimes, patience is a better bet.

Posted by ClueChick at 7:36 AM | Permalink | Comments (2)

One of the very most common questions I get is from men who are in a (closed) marriage or relationship and want my advice on how they can make themselves more attractive to women online. My answer has two parts:

First, all of the advice I give applies to everyone; what makes a single guy attractive -- smarts, competence, attention to detail, sincerity -- are the same things that make a partnered guy attractive. So, there's no call, in my mind, for specialized advice for cheaters.

Second, although I reserve judgement from any individual case of cheating -- I know that each case is likely to be more complicated than I can or would imagine -- I'm against cheating. I don't see it as an honest and healthy way of moving through life, and I think you all know how I feel about honesty. I don't understand why one would want to share one's life with someone with whom you can't share the major ups and downs in your life. And bedroom fun, relational fun, falls into that category for me. Thus, I can't wrap my head around cheating. And I will not, therefore, tailor specialized advice for cheaters to improve their odds.

The one thing I will say is this: If you're cheating, have the integrity to be open about that to your potential paramours. This will decrease your odds, but it will make you less of a scumball, because a woman who doesn't want to get involved in a cheating situation shouldn't end up there by way of trickery. Enough people see it as not-a-big-deal that you should be catching fish in that pond and letting the rest of us make our own choices with regards to this ethical line.

Posted by ClueChick at 10:06 AM | Permalink | Comments (1)

I've been playing with this woman for a few months. It's been fine, but has run its course. What's the best way to end it?

I spend a lot of time talking about the challenges of getting a casual encounter or relationship going, but there's another issue that, apparently, comes up from time to time. What do you do when you have a regular, ongoing thing that you're ready to end? It's casual, so it's not really a breakup per se, and in many casual arrangements, there's no regular date to be broken, but, rather, no new date to be made.

Yes, you can end a casual thing by just dropping it. One of my guys and I make a date every month or two, by IM, and if it went several months without any contact, it wouldn't particularly impact my day to day life. But it would have the unsatisfying effect of being unclear. Is it over, or are we both too busy? This can also leave the other person in the uncomfortable position of getting in touch with you to arrange a date, not realizing that you're done, and then you'll have to have the conversation about it, anyway.

Better to let them know when you've made the decision. Unlike with a more committed romantic relationship, where I would say that breaking up over the phone or via IM would be tacky at best, in a casual engagement, it's fine to end things in the same way that you do most of your date arranging. Do you arrange things over the phone? Give her a call. If you make dates on IM or in email, drop him a line that way.

It's not a big deal, as long as you've both been clear about where things are, and that you have no plans to make it a long term thing, and it's only good form to be clear at the end as well as during. Not to mention, the next person you try to pick up might be a friend of hers, in which case, you're more likely to get somewhere if she knows you're not a loser at the end of things.

Posted by ClueChick at 5:28 PM | Permalink | Comments (0)

This one seems obvious to me, but, like so many things that seem obvious, it turns out not to be. In fact, I've written about it before, but I just got a really awful picture, so I'm inspired again.

First, your photo should be recent, and it should reflect, more or less, how you currently look. To the guy who sends me a picture of himself and says, "But I've lost 100 pounds since then!" -- you might as well not send me a picture, because 100 pounds makes a big difference, so I still have no idea what you look like, but if I'm someone who doesn't like fat guys, I now think you're one.

Second, your photo should show you clearly. I got a picture last week that was so dark that the guy looked like a shadowy, hunchbacked monster. He might have had a beard, or long hair, or been black, but I couldn't tell. Another popular one is the picture from afar. Again, this doesn't help me.

Third, your photo should not focus on your dick. I know that's where you're going to want me to lavish my attentions once we meet, but just pretend for a moment, if you would, that I care about more than that.

I like a photo that shows a man's face clearly, and gives me a sense of his build, though it doesn't have to be a full body picture. I happen to care more about how a person carries himself than what shape his body is, but that carriage is hard to capture in pictures. I've occasionally received an action shot -- him playing a sport or walking or dancing or what have you -- and I tend to like those for that reason, though they often don't have a clear picture of his face, so if that's the case, two pictures isn't a bad idea.

Posted by ClueChick at 7:49 AM | Permalink | Comments (0)

In Setting up a first meeting, I said something sexist, and one of my astute and culinarily talented readers called me on it:

[I wrote:] 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!

[And he critiques:] Look I'm all for encouraging more chivalrous behavior in our society, but I wonder if you're not actually setting up a bit of a double standard... But it strikes me as a little... how to say it... spoiled to expect the guy to "make it easy for her" on a first meeting. All things (and genders) being equal, I think it's important to remember that a first meeting should be made as convenient as possible for both people. While I'm more than happy to go out of my way to meet someone I think is interesting, it tells me (as a guy) something about the woman if she's happy to meet in the middle, as it were.

I'm not trying to be snarky, but it seems that one of the things that is very important to you (and to myself) is the belief that men and women are equal. One of the most distorting assumptions that sneaks its way into erotic negotiations is that the woman brings to the bed (or table, or kitchen counter) something more special, or important, than the guy. You have made a point in the past to explain that women (at least some women) like sex just as much as men. But when a woman expects a man to treat her deferentially, well, then equal enjoyment is not likely to happen.

Unfortunately, he's right.

In writing the original post, I was thinking about those times when there's a guy who really wants to meet me, and about whom I'm sort of lukewarm and not feeling very inspired. In those cases, I'm much more likely to meet him if it's easy and not far out of my way to do so.

As a general practice, however, I'm perfectly happy to meet a guy halfway, or even, sometimes, in his neighborhood, if it's not a huge pain in the ass for me to get there, and I think that's the right and reasonable thing. In the same vein, I expect to split the bill if we get a meal with a single check at the end. (In some ways, even better is to go to a coffee shop where we each pay separately, thus avoiding what is, for some, a loaded moment of "how is the money going to work?")

All that said, because the economy of bodies on CL is so dramatically in favor of the women being picky, you may get a leg up on the competition by being willing to go out of your way, and making it easier for her, and that's what I was thinking about in the initial post. That's still true, and the tension between that and my inclination toward equitable treatment and behavior between the sexes isn't making me happy.

'Nuff said. Thanks, Sid.

Posted by ClueChick at 8:30 PM | Permalink | Comments (2)

One of my handsome and inquisitive readers asks:

What do your friends think?

Before I started my adventures on Craig's List, I was much more tame than I am, now. I tended to be involved in longer-term relationships with a lot of emotional content. About a year ago, I ended a big deal relationship, and I knew I wasn't going to want to be involved in a serious way with anyone for a while, where "a while" has yet to be determined. A couple of months after that breakup, though, I had my first one night stand, totally on the spur of the moment, and it turned out to be a lot of fun. I'd always thought that casual sex wasn't for me, but it turned out that I could enjoy it quite a bit. Thus was born a new phase in my relationship life, yadda yadda.

Most of my friends are (or were, at least) sluttier than I, so, for the most part, they've been extremely supportive about the whole thing, while simultaneously being quite amused. (I, by the way, use "slutty" as a positive descriptor.) I've gotten a lot of good advice from my friends, as well as the occasional, "Are you sure this is a good idea?" when I start to get a little too crazy.

In one case, a friend turns out to have disapproved so much that we're no longer friends. We never got to talk about it, so I don't know if it's that she disapproves of casual sex (despite having had a lot of it herself, but in her younger years) or of me (the previously rather pure friend) having it. I wouldn't have chosen for the friendship to go that way, but I definitely take a love me, accept my choices stance in my friendships.

I like it when my friends call me on my shit, or challenge me to think more critically about something I'm doing or how I'm doing it, but it's also important to me that they a) generally accept my choices and b) can live with it when I don't take their advice. That's true in any number of facets of my life, the ensluttification included.

Posted by ClueChick at 10:24 AM | Permalink | Comments (2)

But do you have any advice for or thoughts about postings outside the usual m4w or w4m? We're a happily-married couple who met on CL and who both like having sex with women ... So, as a single woman, speaking for the smarter set of single women who enjoy CL CE, what's your advice for the less-traditional posting categories? More specifically, what would make you, a smart, sexual, single woman, interested in trying something outside your normal category?

Obviously, not all smart, sexual women posting to CL are bi (or even if not identifying as bi, at least willing to have some bisexual experiences), but a lot of them are, and it doesn't hurt to approach them.

Personally, I love nontraditional hookups. A recent fling commented, "You seem pretty frisky!" and it's true, I am. And I like trying new things, including play with couples. But, simultaneously, I'm quite leery of couples posting to pick up chicks, and I'll explain why.

They fall, typically, into three categories:

First, there are the couples where the guy thinks it would be really hot to be with two women, and he's almost got his wife convinced. If I turn out to be just the thing, maybe he'll actually get some hot girl-on-girl action. Yuck.

Second, there are the couples where they want a third body, but without having another person. I had a couple explain to me that they'd love to get together, but they only kiss each other, and they don't do any penetrative play with the third person. So, basically, I'm there to watch them fuck and to lick their favorite spots. Uh, no.

Third, and the only ones I would even consider sleeping with, are the couples where both partners are actively seeking out a third person, and they want to have someone who's fully participating, not necessarily in the relationship, but certainly in the activities in the bedroom.

If you are in the third category, how do you signal that to a prospective fuckbuddy? For starters, have the woman in your couple do the initial contact. There's nothing that convinces me that she's really, truly interested like actually hearing it from her mouth (or fingers, as the case may be). If you've had prior experiences along these lines, talk about them, what worked well, and what didn't, etc. In general, the same sorts of things that get me interested in a guy will get me interested in any other combination that's up my alley: interesting, engaging, smart people who connect with me as more than simply a collection of holes.

Posted by ClueChick at 7:20 AM | Permalink | Comments (0)

What is my window of time to reply? In other words, do I have to get a response out within the first hour of reading a post? Or within the first two hours? I'm just wondering if there's a point at which a woman will stop reading emails because she's just gotten too many.

This is an interesting question because I haven't thought too much about it. I'd say that there's no particular window, other than non-prime time being between 2 hours and 24 hours after it posted. After 2 hours, my inbox is usually quite full, and I've probably responded to a few to see how they are, so I shelf new responses during that time while waiting to see how the initial conversations go, unless the new response rocks my world.

I actually like the replies that come in a few days after posting an ad, and since, by then, the deluge has turned into a trickle, I actually pay those responses more individual attention than they would get at first glance in the early responses. Unfortunately, these late responses are nearly always dreadful. So, mostly, what that means is that I have more mental space to criticize them.

The fact is, if you have an excellent response, I'll pay attention to you no matter when you write me, but if you want to stand out, either be quick, or be slow.

Posted by ClueChick at 8:57 PM | Permalink | Comments (0)

I think the problem is that I don't understand what a woman would want to get out of non-relationship sex with me. I'm a geek, not at all the alpha male, not at all the pretty boy or the jock or the executive. Women who have simple needs ("I want to be skillfully fucked by an attractive man") are amply served by the large line of more charming, better looking, better performing men who are looking for NSA sex. That's just the nature of the market and my place in it.

So please, help me understand why a woman would pass over the long line of more attractive men who want fuck buddies and choose something closer to home. What are they looking for? What can I give them? What assurances and enticements do they need?

What women want in non-relationship sexual experiences to meet men who like and respect them and want to have sex with them without judging them as sluts or treating them badly for being easy or whatever other ridiculous idea men carry around in their heads about loose women. We don't want to be lied to, we don't want to be pressured and we don't want some fucked up head trip. Basically, we want what guys want: fun sex without hang-ups. It's just that most women have different hang-ups than most men have.

What a woman would want to get out of sex with you is sex with someone she finds attractive and appealing. Lots of women go for geeks (trust me on this one) and are interested in more than a jock-y bod or big expense account. This is a key thing for you to get in your head: you, as you are, are some woman's fantasy, and fit into some women's daydreams. Be assured in that and then it's just a matter of hooking up with the right women!

That said, it's true that there are lots of hot men out there looking for NSA sex, and you may not shine in the one night stand realm (though don't sell yourself short -- you may be just the thing for some women!), but if what you're looking for is casual FWB or fuckbuddies or just an occasional lay with someone you don't have to lay the groundwork with every time, you're in a good position.

Only you know what you have to offer, and if that's compatible with keeping the distance you need. When I'm looking for FWB, I will pass on the superficially hot guy in order to find someone with whom I have more click. You can help yourself avoid that by finding women who are also clearly and explicitly not looking for anything serious.

As for assurances and enticements... I'd say, if you can talk to her like a real person, and offer her the kind of sexual adventure she's looking for, you're off to a good start!

Posted by ClueChick at 9:54 PM | Permalink | Comments (2)

Okay, I'm going to try not to be too snarky, here, because this guy sent me an email but my response to him bounced, so instead, he gets featured here!

I am a 29 year old cute male and have received responses from girls when I post on women seeking men, but never on casual encounters. I work alot and sometimes do not get all my needs met. Am I doing something wrong on CE, are most of the posts fake, are women who post swamped with emails, or is there another site that might be more accomodating to my needs??

First off, you're right, you're very cute, and that's working in your favor. And you obviously are able to string together a coherent thought, so that's good, too. But...

I know there's a lot of cultural support for the idea that men have "needs" that women are supposed to meet. Let's toss that idea out the window, okay? If you're approaching your CE posts from the point of view of what you need from a woman, you're starting in a bad place. I, personally, never respond to posts that are focused around what the guy "needs". In fact, you'll notice I've made some snide remarks in past posts about this, and I certainly will again. You don't need anything from me, or from any other woman, and we don't need to meet those needs or help you out or anything like that.

Lots of posts on CE are fake. All women who post are swamped with emails, and if there is another site that's more accommodating to your needs, I haven't discovered it, yet, though if you're willing to pay for it, most cities provide a vast array of prostitutes who won't care if you think of them as meeting your needs.

Even in a casual encounter, most women don't want to feel like a piece of meat. When you set it up that way, it's not appealing, and it really, really comes through in how you (men, generally) communicate. Think of casual sex as something you're going to be doing with another person. An actual person who has wants and needs of her own. And then think about how to be appealing to a new person. As long as a woman in your eyes is simply a receptacle to discharge your orgasmic urges, you're going to have a hard time capturing their attention.

Posted by ClueChick at 8:12 AM | Permalink | Comments (1)

How do you handle STD discussion/questions?

This is one of my favorite questions, ever! I love it when guys are attentive and knowledgeable about the risks involved in sex, casual or otherwise, which is part of why I love it when a guy doesn't give me a hard time about meeting in a public place before getting together to fuck.

My approach to this is to mention condoms in my ad, for starters, so that right up front, everyone knows where my expectations are. I love it when guys respond including their own take on safer sex practices, and then I like to touch base on it in our initial emails leading up to a face-to-face meeting.

On those occasions that I respond to an ad, I don't always mention my safer sex practices right off the bat, but I do try to work them into the conversation early on.

Usually, guys have been pretty relaxed about talking about these things, though I've gotten some flak for asking questions someone thought were paranoid or excessive. Needless to say, if I get push-back on this, the conversation is over.

I will admit that I have had some hookups where I didn't discuss safer sex beforehand, and in those cases, I just assume we'll use whoever's safer sex rules are more stringent (usually mine). I'm floored, however, by how many men have showed up at my house with no condoms. Are they idiots? Are they simply assuming I'm using some other form of birth control? Do they think they're not just as much at risk of catching an STD as I am? By this point, if it's a guy I really want to fuck, I'll usually get out one of my condoms (which are better for giving head, anyway, because they're non-latex and thus, taste much better), but if I'm even remotely on the fence, I send him packing.

Posted by ClueChick at 7:32 AM | Permalink | Comments (1)

What are your favorite places to meet?

I'm lazy. I like to meet in my neighborhood, or near somewhere that I'm going to be, anyway. Basically, if a guy makes it hard for me to get to where I'm going to meet him, or wants me to go way out of my way, I have to be desperately hot for him to make it happen.

There are a couple of cafes and coffee shops in walking distance to my house, and those are my preferred venues for meeting. Meeting for coffee is nice because it can be a long or short date, depending on how things go, and it's pretty inexpensive. On occasion, I'll meet someone for a meal, usually lunch, since that's both inexpensive and time-limited, as well as being less "loaded" than a dinner date. When the weather's nice, I'm often happy to meet somewhere outside, like a park, though it's nice to have a place to sit down, and having coffee or food gives me something to do with my hands.

I sometimes will meet someone at my house, though I don't necessarily recommend this; it's clearly the less-safe way of doing things, not to mention that if I decide I don't want to fuck him, it's more awkward and difficult to say no. When I do this, I make sure that a roommate or neighbor is home as a safety.

I never meet a guy for the first time at his place. There was a guy this fall who I was unusually hot for, but he was completely unwilling to meet anywhere else. Too bad.

All told, though, meeting at a friendly, low-key coffee shop near my house is far and away my preferred locale to meet someone the first time.

Posted by ClueChick at 8:09 AM | Permalink | Comments (1)

How many responses do you get to a typical ad?

I'm pretty sure I've talked about this in passing in some other post, but I haven't made it the primary topic of a post before. So! How many responses does a woman get when she posts in the CE section of Craig's List?

A lot. Typically, I can count on about 100. I have, on one occasion, managed to write an ad that garnered only 25 or so responses, and they all sucked, which was appropriate, because the ad sucked. But most of my ads get between 90 and 150 responses, most of those in the first 24 hours. Once, on a whim, I posted the trolliest ad I could come up with while still being honest about who I am and what I'm looking for, and I got almost 300, and nearly all of them blew.

I find that I'm happiest with my responses when I write a long-ish ad with a lot of (usually nonexplicit) detail, which seems to signal that a) I'm for real and b) I care about guys taking the time to write good responses. In these cases, I've tended to get 80-120 responses, about half of them good (where good means that it's not obviously generic and the guy seems at least moderately clueful), and roughly 10-15 of them are promising enough for me to get my hopes up.

Posted by ClueChick at 8:48 AM | Permalink | Comments (0)

One of my fabulous readers writes:

I'm a good person, honest man, hard working, gentle, nice, and friendly. Is this the problem? Do I need to pass myself off as "the bad guy" or "the tough guy" in order to get laid? I'm not sure what I am doing wrong.

No, no, no! A thousand times no! Ugh!

Okay, okay, I know that bad guys seem to get more action with the ladies, but would it really be worth getting laid if you had to a) fake yourself and b) become a person you respect less in the process? Yuck!

It's possible that I have strong feelings about this one. But, really, you don't have to be a bad boy to have casual sex. On the other hand, no, you shouldn't be a pushover. Very few women go for pushovers, and most of them are women you wouldn't want to get too involved with.

It's an unfortunate thing that confidence is so often associated with jerkiness; nice guys, this is your big chance to change the world: be confident and be nice! Be secure in yourself and your way of being in the world. Being confident, not being "bad" or "tough" is the way to go.

Posted by ClueChick at 10:09 PM | Permalink | Comments (2)

One of my charming and handsome readers writes:

Is it foolish to hope that these email and IM exchanges could turn into meetings? I know there's no blanket answer, and that every woman is different. But in general, do you think that women looking for virtual sex on CE are interested in the real thing? If so, do you have any tips on making that transition?

To which I initially responded that this is a realm where I don't have a ton of experience, since I normally post for hookups, not for email exchanges, so I asked around a bit, and here's what I've come up with:

Women who post to CL are, generally, less inclined to meet than men are, even if they post an ad that's geared toward meeting. There are a number of reasons for this: One of the things that seems to hold women back is the fact that they're afraid that they're better online than in person. Keeping it online is much safer -- they don't risk the same kind of rejection, not to mention the actual work involved in leaving the comfort and security of their own desk/couch/bed. Often people posting to CL are doing so because they're very shy/tentative in person. Additionally, for women, there's the unfortunate social stigma of being seen as "loose" or "easy". I'm lucky not to be hung up on that, but I'd have to be blind not to see it, both in how some men (and women) respond to me and in how women talk about hookups and the associated social implications of them.

That said, some women who post just for erotic email exchanges ARE interested in getting together, if there's a click, but that can be a big hurdle for some people, taking it offline and into real space.

So, no, it's not foolish to hope that such exchanges can turn into meetings, but it would be foolish to pin too much hope to this. Women looking for virtual sex are ABSOLUTELY interested in the real thing, but they may, for any number of reasons, not be willing/interested in making that happen. Remember, everyone, women like sex. We just get a shitload of pressure to be "good girls", so it's a hugely loaded issue, especially when it comes to NSA sex.

As far as making the transition, this is a bit of a shot in the dark, but here's some of what might work for me in that situation. Don't make your continued email/IM contact contingent upon meeting, and try to avoid coming off as though you're putting pressure on her. Express your interest firmly and clearly but without expectation of reciprocity. And by all means, you should use what you know about her interests and leanings to suggest what fun it might be. You have a leg up on any potential competition because you've gotten to know her without being a total mack, in the context of a mutually engaging email conversation, and that's a good thing.

Posted by ClueChick at 7:39 AM | Permalink | Comments (2)

I have a book/picture/email/ad that I'm wondering if you would review?

Yes, of course! That's at least half of the point of this blog, after all: to answer the weird questions about dating and the online scene that you can't ask anyone else. Are you wondering which of your three dreadful pictures is the least dreadful? You think your email has game, but you're not getting any responses? Just curious about a particular dating/attitude book? I'm your girl chick!

Obviously, in some of these cases, especially photographs, I won't be able to share my nuggets of insight with everyone, but as trends in questions develop, I'll be able to pass those on.

Why am I doing this? Well, aside from enjoying both lending a hand and the whole personal ad scene, I presume that in a vacuum, I will eventually run out of opinions (hard to believe) and have to start recycling old posts. So, by all means, feel free to ask me whatever questions you might have!

In upcoming posts, I'll be reviewing Play or Be Played: What Every Female Should Know About Men, Dating and Relationships by Tariq "K-Flex" Nasheed and, once I actually get my hands on a copy, The Game: Penetrating the Secret Society of Pickup Artists by Neil Strauss.

Posted by ClueChick at 9:22 AM | Permalink | Comments (0)

Today was an excellent mail day, and I have lots of interesting things to ponder and then post for your reading pleasure. For now, I'd like to start with a question one reader asked:

What's wrong with reposting? Writing a good post can take anywhere from an hour, if you're inspired, to half a day. Why not get the most out of it?

First off, if you're writing posts that are getting you a good response rate, you don't need my advice. In fact, if you're a man writing ads that are steadily getting you more than a couple of replies each time to post it, I'd love to hear about it, because you're in a vanishingly small minority. Everything I write here is from the point of view of a woman who loves Craig's List for all its potential; I've never tried posting as a man, much less tried posting enough times to get any useful collection of data on this point. I have the bright idea of banding together my male readership to put together a slightly broader range of information on this point, maybe after the new year rolls in, but for now, I'm just writing what I know, which is a woman's perspective.

That said, the reasons I recommend against reposting are:

1) If you're reposting daily, you look desperate. Desperation, as we all know, is never attractive.
2) Women who browse CL frequently will recognize your post from prior days. If your ad is one that she might have been inclined to answer, she will be less inclined to answer if it's posted often.
3) If you're posting frequently and not getting the responses you'd like, posting more frequently is unlikely to help.

I'm not saying you can't post every day. I'm saying that if you do, you should mix it up a bit. It's a rare post that can't use a bit of spiffing up, and sometimes taking a different tack will help you to appeal to a different audience.

Also, reposting the same thing every week or two is significantly less desperate-seeming than posting on a daily basis. Try having a few ads that reflect what you want and who you are, and alternate posting them, so you're not "that one guy" to the women who are paying attention. Variety is, after all, the spice of life!

[Private to errand boy: try volunteering some information and see what the lady says.]

Posted by ClueChick at 11:19 PM | Permalink | Comments (0)

I respond to all the w4m posts in my citys casual encounters section and have been for months but I've only heard back from one person. And that was a GUY who was hoping I'd be into him!!! What am I doing wrong?

Without seeing your emails, I can't pick them apart for all the things I'd change, but I bet there's a lot. If you're responding to loads of ads, you're probably sending a pretty generic response to all of them, and that's not very exciting. Furthermore, if you're responding to every last w4m ad in CE, some of the people you're responding to are a) men (as you've discovered), b) bots, collecting email addresses for future spam and c) women who are looking for something very specific, and you're not it.

I've been posting the occasional ad for several months, and there's one guy who reliably responds to every single post I make, regardless of what I say I'm looking for. If I want a hot weekend tryst, he's my man. If I want something regular for the next few months, he's my man again! The problem is, he sends the same email every time, and every time, that email tells me that he's looking for something that doesn't match well with what I want.

Rather than respond to every w4m ad you see with a generic email, I suggest that you take a bit of time to skim the ads before responding. The bot ads should literally leap out at you in most cases. Many times, the fake ads by men will, too, though not always. Look for ads that sound like a real woman. Practice will help on this front.

Once you've found an ad by what sounds like a real woman, make a note of what she wants. Is she an older domme looking for younger boys to humiliate? If your thing is younger women who like to have their ass slapped, you're going to look ridiculous if you email her. If you're flexible in your desires, say so. Or, better yet, do a bit of tailoring for each ad you respond to.

It's okay to have some generic text in your email, a bit about you that you can always cut and paste, but it's worth spending a couple of minutes making personalized additions to show that you're responding to a specific ad and to help her know that you're really a good fit, beyond just having a dick.

Posted by ClueChick at 9:46 AM | Permalink | Comments (0)

In I'm not confident. What do I do?, I gave some tips about growing one's confidence, to which, one of my readers responded, "See, I am confident. Just not on dates. I'm better at doing lots of things than I am at flirting, so I have no confidence there, and it shows!"

First, I'd like to thank this anonymous commenter, because he has rightly pointed out that I took the easy way out of the question of how to build confidence. Also, he raises the good question of what men (or anyone, really) who are generally confident should do when that confidence doesn't extend to the dating/flirting/hookup scene.

The truth is -- and this shouldn't surprise anyone -- building confidence isn't easy. People who lack confidence, regardless of the specific arena, usually have years and years of insecurity to sort through in order to lay a solid foundation on this front. So, if you're looking for a quick fix, you might try hypnosis. I have no idea if it works, but, what the hell, right?

My best advice for people looking to build confidence in any realm is to get out there and practice. Be prepared to flail and fail, because this is a skill that doesn't necessarily come built-in for many people.

When it comes to flirting, I suggest starting with your friends. This worked spectacularly for me -- I have several friends with whom I can be very flirtatious, and they back, and we all understand that it's without intent. Make an explicit agreement with a friend or two that you'll play around with flirtatious comments and the like. This brings it into your day-to-day interaction without the enormous pressure of doing it with someone you hope to impress.

Another possibility is to watch people whose social technique you admire. You can think about what they do and how they do it, and then you can "try on" their approach. Pretend you're them for an evening. (A note here: I don't actually mean you should pretend to be someone else, because I (nearly) always advocate honesty. What I mean is more like an acting technique to try to get into the character of someone who's already confident in the dating scene.)

I'll be expanding on these thoughts and including others in future posts, so keep an eye out for that. In the meantime, if any of my readers have made the transition from lack of confidence to high confidence in the flirting arena, share the wealth! How did you do it? What helped? What hurt?

Finally, there are some books out there on this topic, but I haven't read them, yet, so I'm not going to make any recommendations. Look for those down the line.

Posted by ClueChick at 8:54 AM | Permalink | Comments (1)

You say physical attractiveness isn't everything. But I'm not physically attractive and I'm not confidence [sic]. What should I do?

Are you serious? You are, I can tell. Well, you'll probably hate this answer, then:

Get confident.

Yes, that's all. Simple, huh?

Okay, so it's not just a light switch. But that's the end goal, and we have to agree on that. We also have to agree that you have some characteristics that are worth being confident about. If you think that you have no reason to be confident -- you're ugly, dumb, unfunny, clumsy, awkward, smell funny and furthermore can't learn anything much less better yourself -- we're done. Do not pass GO, do not collect $200.

If you don't think all those things about yourself, if you think there's a glimmer of hope for you to build your confidence, then you've got something to work with. Start there. What are your strengths? Maybe you're a kickass cook? Why not go to some cooking classes to increase your range? Start a dinner club with friends to trade off throwing fancy dinners? At the very least, you'll get out of the house and have some fun. And at the end of it, you'll be more confident in your cooking skills. That doesn't hurt.

By improving yourself and playing up your strengths -- both to yourself and to others -- you can gain confidence in yourself, and that will make you more attractive. But the big benefit, if you do it right, is that this confidence will help you need less of that external validation, because you'll know you're worth it regardless of who's sleeping with you or who isn't.

Don't improve yourself because you think it'll get you laid more, though. That's a quick-fix and doesn't solve the deep-down problem, which is that you're looking for others to feed you the support and validation that you need to provide yourself. When you're solid in yourself, everything -- and I mean everything -- is easier.

The most attractive people are the ones who aren't using me as a crutch to prop up their fragile egos. That's your goal.

Posted by ClueChick at 10:04 AM | Permalink | Comments (1)

I don't respond to a whole lot of ads, and when I
do, I make sure that I think we're a good match. My
question is if I should definitely send a photo with
my emails or should I wait for the woman to ask for
one or to send me hers?

Unlike some questions I receive, this one doesn't have a single hard-and-fast answer. If you're drop-dead gorgeous, it probably won't hurt for you to send a photograph, unless the woman is very insecure and decides you're out of her league. In that case -- and I may be a bitch for saying this -- but good riddance. I don't say that because I don't think unattractive people should get laid but because I don't have a lot of patience for people who rate themselves so poorly (look for more on this tomorrow). If you're the type who really relishes being with people who are insecure, then this is your loss and you may want to hold off on sending a photograph until after she sends hers so she knows that even after seeing her pic, you're interested.

In general, though, if you're reasonably attractive, it is quite unlikely to hurt your chances of a successful approach, and there's a good chance that it will, in fact, help. I never respond to someone solely on the strength of his pic, but a good pic can make me more likely to respond to someone whose email is on the edge.

On the other hand, if your email sucks, it won't matter how attractive you look in your picture, because I'm just not visually-oriented enough that having a hot guy in my bed is going to offset the fact that he's deadly dull. And if you write me a good email but don't send a photo, I won't ding you for that. In fact, I would say approximately half of the people who have responded to my ads have not sent photographs, so it won't even be conspicuous if you do or do not send one.

If you're quite plain, don't photograph well, or are downright unattractive, you're in a tough spot, as you've probably noticed. I, like most women, am loathe to sound shallow, but if your photograph makes me recoil, your fabulously brilliant email is unlikely to be enough to get me over that reaction. I don't like this about myself, but I've come to terms with it. In your case, I suggest one of two possible approaches:

The first option is to include your photograph with your email and hope that it will eventually reach a woman who's into ugly, or who's more seduced by words than I am. This approach will save you the false hope of some exciting emails if she's only going to reject you later because you're funny-looking.

The second option is not to include your photograph and hope that by the time you do get around to exchanging pics, she'll be into you enough for your brain that your freakishly large nose or snaggleteeth won't be an impediment to a hot and sweaty rendezvous.

If you're not ugly but are just plain, I'd suggest the second approach, and I'd also suggest that you not bother looking online for hookups. Looking online for something serious, people look more for personality than looks, and in that case you may shine.

I don't know which of these approaches, for ugly guys, will work better, because I'm afraid that neither of them works with me. Hey, I admitted I'm shallow. I don't have to like it, but I don't have to make myself a liar over it, either.

Posted by ClueChick at 5:56 PM | Permalink | Comments (2)

A reader wrote me this:

I write really good responses to women's posts on CL and profiles
on other sites. I read what they write and then i respond to specific
things they say. I try to be funny, but not too goofy, respectful, and
not creepy. I almost never get a response to my emails, though.
What gives?

Never let it be said that picking up women is easy. Whether you're looking for casual sex or a more serious relationship, it can be very tough to navigate these waters, and you have my deepest sympathy. Picking up women online has many unique challenges.

First, you never know how serious a woman is. Perhaps this is a profile she wrote two years ago, before she found her current boyfriend, but she hasn't taken it down because she likes the ego boost of having men respond to her. Maybe she posted to CL because wanted to see "what's out there" without leaving the comfort of her couch. She might even think that she's serious, but when it gets right down to actually going to the trouble of responding to people's emails, she discovers she's just not that interested. (I've pulled all of these, I'm sorry to say.) If any of these are the case with a woman you contact, you won't hear back from her, and it has nothing to do with you. Don't take it personally.

Second, you never know a woman is really a woman. This is more the case on CL (especially the CE section) than on actual personals sites, I believe, but sometimes the posts from women are posts from men hoping to get lots of pictures of cocks and bods. Others are business opportunities for porn sites and webcam operators. (These are usually so painfully obvious that anyone who responds to them deserves the spam he'll get as a result.) Don't take it personally.

Third, you never know how much email a woman is getting in response to her post or profile. When I post to CL, I get a minimum of 75 email responses, the bulk of them in the first two days. Most of my ads garner about 150 - 250 responses over the course of the week that they stay up. That's a shitload of email. Some of them shout out their lack of appeal: the ones that are just stats, or maybe just a picture of dick, no text included at all, or the badly worded, awkward married guys who are hoping for a quickie that afternoon. And others are so over-the-top appealing that responding to them is easy. But a lot of them are good, solid, interesting responses that I can't possibly do justice because of the massive influx of email my post generates. I am absolutely positive that I have passed up great opportunities because their email got lost in the shuffle. Don't take it personally.

You might be sensing a trend here. It's important not to take a lack of response to your email personally, because 9 times out of 10, or even 95 times out of 100, it's a matter of circumstances beyond your control. Don't kill yourself writing the perfect response to 10 women a day, because you'll exhaust yourself, mentally and emotionally. Try to approach it with good humor, and if you find yourself getting bummed out about the long odds, take a break. A lack of response isn't a rejection (and I'll talk more about rejection in a later post), and you'll do well to consider it a lucky break; if she doesn't respond to you, she's obviously not a good fit for you after all, no matter how good her post or profile sounded!

Posted by ClueChick at 1:17 PM | Permalink | Comments (0)

One of the most common questions/complaints about Craig's List, especially the Casual Encounters section, is, "Are there any women out there? If I post an ad, will an actual woman ever read it? Those rare w4m ads... are they really women?" Naturally, it's not as simple an answer as you might like.

First, obviously, yes, there are women out there. I'm one of them, and I know some others, too. We do read some of your ads, and we also respond to some of them. Furthermore, we post our own ads and read the responses we get.

That said, lots of the purported women are not really women. This is a fact of life on the internet, and if it's going to piss you off, you should stick to interacting with people face-to-face. If you post an appealing ad, there's a reasonable chance that you will hear from a bold fellow who figures it's worth a shot to see if you're bi, or, at least, heteroflexible. And some of the w4m posts are written by men hoping to get some nice pictures. Others are written by webcam businesses to snag your email address and spam you with offers to view their cam, for a small fee, of course.

It's not always easy to distinguish the "real" women from the posers and spammers, but we're out there.

Posted by ClueChick at 6:33 PM | Permalink | Comments (0)