Dear Cluechick: Cooking classes won't help!
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.

Comments
"When it comes to flirting, I suggest starting with your friends."
Oh God that sounds like a recipe for disaster.
Posted by: Ben | December 21, 2005 2:23 PM