How you do it matters, but what's so much more important is that you simply *do it*, again and again and again. You'll get rejected, of course, but you will also get better at it and more confident. Ask questions. Start up a genuine conversation about a topic at hand (Ex: If you're at an art gallery, ask her if she thinks the paintings are as lame as you do). Compliment her nails, her outfit, her hair, stuff she has control over; in other words, don't comment on her eyes, ass, boobs, etc. Smile; not like a creep, just like someone who is at ease and happy to be there. Be funny, if possible. Don't be a jackass. And, I repeat, do this again and again and again. You know how to get to Carnegie Hall?