It’s a tricky situation, but dating your friend’s ex can be done. It just takes understanding from all parties involved…a lot of understanding. The main thing to take into consideration is whether or not you are willing to sacrifice a lifelong friendship for a boyfriend (or girlfriend)? On the flipside of that, are you willing to sacrifice a new relationship for a lifelong friendship? It is a very complicated situation and there’s a field of emotional landmines that you have to walk through before you get a final answer. Bottom line: be an adult about it and think with a clear head. You don’t want to lose a best friend AND a potential relationship. That wouldn’t be fun.