I know that it's harder than just seducing a woman who isn't on the job, but I currently live in an area which has a much less active nightlife when college is out. I found a bar with an attractive bartender, though, so I thought I might as well try to get a FWB situation with her. If I get to know her better and I like her, a relationship could work too.

My general strategy is to be a regular at this bar, come at least once a week to chat with her, other bartenders, and other customers. I did this last night, since I know it's weird to just hyperfocus on the attractive girl, and there were people who started chatting with me too.

I expect she probably has a boyfriend, but even so, I think that if I make a good impression on her and other bartenders I can at least leverage that when college is back in session. Never tried it before, but I've had friends who said that being friendly with bartenders helped them when trying to chat up girls.

Anyway, if she does happen to be single, how do people suggest I approach this? Should I leave larger tips for her than other bartenders? Not every time I get a drink, but every once in a while so I stick out in her mind.

When should I ask for a number or to meet up outside of her job? After a few weeks? A couple months?