When friends date, does it ever work out?

first, welcome to fluther. second, as is the problem with most relationship questions, you really cannot generalize. sometime friends who become lovers works out…sometimes not. in your case, it seems it might (and i say this with very limited information of you, her and your relationship). But if she recently got out of her relationship, you should wait for a bit because you don’t want to be the rebound and you also want her to be able to revitalize herself, emotionally.

Don’t forget many girls just have a ‘flirtatious’ personality, and many people embarass themselves thinking a girl likes them and asking them out, yet they get turned down because she’s naturally a flirter although it doesn’t mean they like someone. It’s always worth a try, but don’t think she’s going to fall into your lap just because she’s a charmer. Go for it and just remember that if she doesn’t accept the offer, you always have more time and more women.

I did that once, pretty much the exact same situation. Didn’t work out, but we’re still best friends, and sometimes we talk about “that thing we had”