There is something about this that skeeves me out as well, and it's not simply discomfort at the idea of doing it. It's the idea of manipulating others for drinks. It reminds me of begging, almost, the whole trying to get free stuff from others. Also, it sounds like leading men on far enough to get them to buy you a drink; it sounds like making them think you're interested, even if you don't actually promise anything. I'm not so fond of things that might inconvenience others, nor the idea of getting drinks from others because I've led them to believe something false.

I believe the male version is to get a girl's phone number? What skills does this require? I'd guess confidence, the art of conversation, body language, assertiveness, initiative, etc etc. Everything that's already been listed. However, what skills does convincing a man to buy a girl a drink require? What would make a man want to buy a girl a drink? I'm getting the impression of a great deal of flirtatiousness.

I feel that a more equivalent challenge would be for a girl to get a man to accompany her to one of her hobbies, like a knitting group or an orchestra concert or a rationalists' meetup. That way, she has to present her hobby well, get the guy interested, and he has to be interested in something other than sleeping with her. It will require more communication than sexuality, and I feel it will teach the desired social skills better.