Worst experiences: In Need of Therapy
So, this guy did enough of the right things (we all know what they are, right? He wrote an intelligent, appealing response to my ad that indicated that he was interested in me, not just any woman who might have posted that day, etc), for me to write back, initially, and then, after several emails back and forth, seeming to connect in interesting ways, I was inspired to arrange to meet him. He lives on the other side of town from me, but he was willing to come to my neighborhood to meet for lunch.
We met at my favorite local coffee shop and then went across the street to the diner for lunch. His assured email persona was much more timid in person, which seems to be a common feature, and one I can understand; interactions online carry a lot less risk, and they're also easier, because they're so one-dimensional, just text on a screen. However, this shift is one of the things that is a big turnoff for me; I tend to prefer confident people to begin with, and then when the lack of confidence in person contrasts with the prior confidence online, it's just not pretty.
But then things went downhill, because his primary topic of conversation is how he used to hang out with all these people who are interested in bands, and he's gone beyond that, and what he likes about me is that I seem like someone who would be really good for him to know.
...
I like to think that I'm a good person to know, and that I can help my friends with all sorts of growth and changes in their lives. This is not, however, the dynamic I want in my casual sex. I want someone to find me good in bed, but not necessarily "good to know" in the sense of major personal change, like finding a whole new friends group.
The conversation continued into how he's really finding out who he is and trying to meet new people who can help him with that...
It was soon clear that when I said "casual encounters", he read "new guide on life path". I'm not sure how that happened, but it did. Lunch was, thus, rather awkward. But it wasn't very awkward until he asked if I wanted to spend the afternoon with him (earlier, I had, foolishly, mentioned that I had the afternoon free). I don't mind turning people down, and I try to do so gently -- "I've really enjoyed meeting you, but I don't see this going anywhere" -- but there's no good way to keep the conversation going after that, obviously, and so I like to have that exchange after we've payed the check.
So, guys, save yourselves some awkwardness and hold the "what next" conversation until you're actually moving on to what next.

Comments
More accurately phrased "Ladies, always have an escape route lined up after a date." Really, the mistake here was yours for giving him the view of your free afternoon, and thus blocking off your elegant escape route. I actually think it is reasonable to start some discussion of what happens next before the check is paid, or at least before you've walked her to her car, because otherwise there can be awkwardness of a different kind. (Speaking from experience, of course. :-)
Posted by: sapiophile | January 27, 2006 5:34 PM
I agree. Sounded waaaaay too needy. Not attractive at all.
Posted by: A | February 7, 2006 4:35 PM