Courting Disaster, Aug 18, 2006

I’ve tried asking out women from my daily routine (college), but that always somehow ends up in friendship and nothing else. To be honest, “always” is probably not the right word, because I’ve only really got over enough of my shyness to actually ask women out in the last year, but in the three cases so far, that’s what happened, friendship.

Going to a bar/party/concert and trying to pick up a random woman doesn’t seem like it would work, first because of my shyness and also because I wouldn’t even know what to do or what to say. The whole thing just seems forced and unnatural… Plus, it seems to me that these kinds of places are just for people looking for a one-time thing. While I wouldn’t mind making out with a hot stranger and never seeing her again, what I actually wanted was to have a relationship, you know?

So, what should I do? Are there any good places for a somewhat shy guy to meet single women? Is there any way to do so outside the whole bar/party context, maybe in an environment where there’s less pressure?

Also, you must have noticed by my post that I’m pretty desperate at the moment, but letting people know you’re desperate doesn’t make you much attractive, so I often cover it up, but then people get the impression I’m aloof, distant, even snobbish. What can I do to stay away from both extremes?