Breaking “The Code”: Is It Ever Okay To Date Your Friend’s Ex?

6. Test the Waters

Okay, so you’re not sure if you have the type of friendship that can sustain anything; you don’t want to lose her friendship but you’re also not sure you’re willing to give HIM up either. Rather than sneaking around with him, why not test the waters with her first to gauge her feelings on the subject? For example, say something like “I know you and John haven’t dated in eons, and you two are (not) still cool, but would you have a problem if he and and one of your friends started dating?” Or you could simply ask her how she feels about her friends dating an ex of hers. If she says she’s cool with it, read her body language to determine if she really means it or if she’s just saying that to appear “evolved” or “mature.” Most men and women, no matter how “cool” they try to be, would have a real problem with this whether they want to admit it or not. However, if she says she would never approve and would cut a chick who even thought about dating her ex, then you have your answer and you can decide how you want to proceed from there.  Some women may qualify their answer, saying it depends on which ex, how long ago they dated, how serious it was, etc. If the ex that you have your eyes on falls into the “it wasn’t that serious, you can have him” category, then tell her then and there that you sense an interest between you two. But if he was one of the biggest heartbreaks of her life, then stay away from him.