Don't invest too much in potential hookups
Hookups are so flukey that it's a wonder any of them actually happen, ever. This is especially true of hookups that you arrange online. After all, if you're horny and she's horny, and you're physically together to start with, because you're at a bar or what have you, the energy you need to get over the inertia of making it happen is relatively low.
Online hookups required more energy to make them happen, since you're probably both comfortable at home while you're making that initial contact. The tendency is to look for something that's going to be hot and easy, and if it doesn't seem like it's going to be hot enough to bother putting on your shoes and heading out to meet, you might not bother making it happen, or she might not.
The vast majority of potential hookups that I start online never come to fruition. This may be because of him or me or circumstances or who knows what, but it's good to be aware that just because you're in touch with a woman and talking about the potential details of a hookup doesn't mean you're actually in the door.
This was a tough lesson for me to learn. When I first started arranging hookups, I would get all excited about this guy or that one with whom I had amazing "chemistry" via email or chat. We'd talk about fantasies and share favorite porn with each other, and I just couldn't wait until we actually got together! Then, of course, things would happen and the communications would peter out, or the dates would keep getting pushed back, or not made at all, and eventually we'd stop chatting and I'd be all disappointed.
Now, I look at this initial flirtation as a thing unto itself. It's not guaranteed to get me laid, but if it does lead to that, we're sharing important information about the things we like. And if it doesn't, well, I've had a fun chat or two with a stranger. And maybe I learned a trick or two along the way!

Comments
Good advice, and a lesson I had to learn myself when I started doing this back in the early 90s. These days, I'm extremely skeptical (to myself) about any new possible hookup until it actually happens. And I admit, there have been times when I started something, and the more I got to know about the other person the less interested I became, and I backed out. And I wasn't always polite about it, especially in the early days.
Thing I came to realize though was that the ones who vanished on me either weren't serious or weren't interested in what I had to offer. Having been on both sides, I'm more understanding when it happens to me, and less disappointed.
Posted by: Rob | September 5, 2006 2:17 AM
Hey Cluechick,
First of all, thanks for your help. I'm a boy on the other side of the planet who has made some real progress on the web hook-up scene for the first time. I was already doing a lot of what you advise, but I found the tips on flirting in emails very helpful. So the initial contact has turned into something quite intense, with some very nice phone sex, swapping pics, sweet conversations etc. As you mention in this particular post, I'm not betting the farm (as you yanks might say) on what might happen. We are in different cities and we can't meet for some weeks. We have firm plans to meet, but I'm aware that three weeks more flirting is either going to tease us both into distraction (nice) or one of us may get bored and lose interest. I'm good at making with the sweet (comes naturally), but not so much with the edge I feel might be needed to hold her attention longer term. So question is, how to challenge her...without being a dick?
Posted by: Mi Ti | September 21, 2006 3:32 PM