One thing that helped me a lot: investing some money in some salsa dancing lessons. First of all, I actually enjoy it, it's fun (if you don't like it you wont' get far). Second, it's sort of cool, compared to, say, talking about startups and computers with someone who is potentially not interested in either one. Also, it's something where practice does pay off, and where you can't fake it, so investing some time will get you results. It's a real dance, too, between a man and a woman (well, a couple in any case, but we'll leave out the PC stuff for the sake of convenience) where the man leads and the woman follows, and they hold on to one another, not one of those flaily club type dance things. You can learn a lot about someone in a 2 or 3 minute dance with them, actually, and if you go to the right sort of clubs, people often change partners, so you have the chance to dance with lots of different people (so it's sort of like speed dating, but not so silly) and see what works out. Most places I've ever been to, people are having fun and smile, which I find a lot more attractive than the pouty, I'm-too-cool look. Oh, and finally, women who know how to really dance salsa are hot. Moving and swaying like that really adds something! Getting up the confidence to ask people to dance is really good too. You'll get shot down lots too, but you learn to deal with that.