My best friend "dated" this guy last year. He tried to get her to go out with him for years, and finally got up the courage to ask her. She said yes even though she didn't like him, they went out twice and then she broke up with him. He and my friend have been avoiding each other for the last six months. He and I have been hanging out for a couple months now as friends but I like him as more than that. Is it possible that he likes me? And would it cross the line to go out with him if he asked?
It's possible that he likes you more than a friend but as he tried for years to go out with your friend - that's a long time! - he might still have feelings for her and he's hanging out with you in the hopes that you'll put in a "good word" for him, with your friend (so she'll hopefully give him another chance).
Even if this isn't the case, if he doesn't ask you out on a date, he might only see you as a friend.
Even though your friend broke up with him, I think it would be polite to talk to her first and see if she's okay with you doing anything about your feelings for this boy - just as a courtesy.Free from:
~~ Happy Day. ~~
at the end of the day you are the one to make decisions for yourself and no one else should be able to control that decision. however this whole societal taboo of dating your best friend's ex I find stupid like if you like someone you should be able to ask them out. but just for your friend's sake you have to tell them as early as possible just as you would if you liked any other guy so that you guys can treat it as something not out of the ordinary.
At the end of the day, the decision's entirely yours. If it were me and I valued my friendship, I would probably just ask my best friend something along the lines of "Hey, I think I really like <this person>, would it be okay with you if I asked her/him out on a date?" Or something along those lines or a variation thereof. This shows a few things: 1) you care about your friendship, 2) you let your friend know you are interested in his ex. If you try to keep it a secret it might not turn out too well, your best friend may no longer be your best friend, and all for a relationship that may or may not even end up working for the long term. Good luck.