Ask A Guy: Is It Okay To Date An Ex-Boyfriend’s Friend?

Hey Joel,

SO a few months ago my boyfriend of two years and I split… and it wasn’t pretty. We are friends now, but there is still some clear tension between us. MEANWHILE, I have started showing interest in a mutual friend of ours. I do not know whether or not he is interested, but he was my shoulder through the breakup and has been with me through a lot. The friend and my ex are pretty close. Is it a bad idea to pursue anything with the friend?

Friends of The Ex can be very tricky, and because there are so many factors, there’s really no hard rule on how to go about the situation. It is going to take a lot of understanding in terms of how your ex feels about you and how strong his friendship is with the guy you’re interested in. But there are a few points you should consider:

First and foremost, your ex doesn’t really get a say in terms of who you can and can’t date. You two are done, and it’s been years since you were a thing. If he tries to intervene and keep you away from his friend, you go right ahead and put him in his place. He had his chance, it didn’t work – case closed.

HOWEVER (and it is a big however), guys dating the ex of a friend is one of the unspoken grey areas in what most call “Guy Code.” If you and your ex were together for a long time, this will make it even more complicated. Even the idea of a friend dating your ex can give you all sorts of odd feelings, and that becoming a reality can make for very uncomfortable conversations and broken friendships.

Digging a bit deeper, this guy you’re interested in has a pretty big advantage, since he was the “good” guy when you were going through your breakup. While you may not have realized it right away, you might have unintentionally idealized this guy because he was your escape and safety. Think back to how you felt about him BEFORE the breakup, and you’ll get a much more honest read on what your heart thinks.

At the same time, do you really want to force this guy to basically choose between you and his friend? That in itself isn’t the best way to start a relationship, and you also stand to lose more people in your life if things go wrong.

In the end, there’s really nothing wrong with you wanting to pursue this guy, but unless he has something super-special that you can’t find elsewhere, it’s probably best to just stay friends.

Best of luck!
Joel

Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube.. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

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