NEW AGE-- I didn't mean to be insulting or anything. The things you said to her just didn't sound fluid. Sometimes when people are doing routines it can sound scripted or can come across as trying too hard. As far as things to say, I would have picked one topic at a time. I wouldn't try to squeeze in her going to clubs and her schooling at the same time. I'd pick one and go with it. That way you have something to fall back on after the first topic is used up and also so you don't shoot your wad in the first or 2nd reply. In her case, since she liked bars and clubs. I'd talk about that. here is an example
"Oh so I see that you like the nightlife. Seeing that you are from "enter city or part of city", what would be the one club that I should definitely stay away from and what would be the one club that would be a must to go to? With this one that you like so much, how is the experience there different than going to just some random club?"
but she will tell you about the club she likes and since she likes it there she will have positive thoughts adn vibes because she's thinking of it. also, when she tells you of the crummy bar, it gives you a chance to talk of it too.
let's say she tells you that she loves "Club ABC' and hates "Club XYZ", this opens things up a bit. no matter what her reason she hates "Club XYZ" it gives you a chance to needle her a bit. like the following.
"Oh so you don't like Club XYZ? It sounds like something happened there. There has to be a story to this! Is this where you go to pick fights? the first thing about fight club is you don't talk about fight club.

you're a little thing but I kind of had a hunch you had a rough exterior.

Omg I went and met a brawler. I knew i shouldn't have quit going to karate lessons. Am i going to have to carry pepper spray for when we hang out?"
make sure that you use emoticons so she knows you are joking and don't think she's manly. but you'd have her laughing more than likely then i'd think you can go from there.