If you have fun going there, then don't ask her out. We'd always go to this one place...turns out one of them liked my friend alot. She'd hook us up all the time...so one day she invited us to her bday, they were both drunk...made out and she wanted to bang him in the bathroom. He declined......few months later an even hotter bartender starts working there. She digs him too, now it's one big clusterfuck and the original chick doesn't hook us up at all and hates the newer chick.
Bro, sounds like your buddy is a fanny bandit, bro.