Ask A Guy: Is It Okay To Date Your Best Friend’s Long-Term Ex?

Photo Source: iStock

Photo Source: iStock

Hey Joel,

So my BEST friend was with her boyfriend for 3 years. About 6 months ago they split up. Me and him have been close because of their relationship. We’ve spoke ever since they split up, but kept in on the down low (because she would’ve freaked!) It’s so strange having a crush and hiding it from her. I really like him, and he likes me. I know she’d probably say she’s cool with it, but I’m not so sure. Is it okay to date your best friend’s ex?!

The answer here is extremely simple, but you’re not going to like it at all. Under no circumstances is it cool to try and get with your best friend’s ex – let alone after just a few months. Especially given the fact that they were together for years, he is even more off limits than usual.

Even in your question you are clearly torn on what her reaction would be if she found out you two have been getting friendly behind her back. While you say she’d probably be cool with it, you also admitted that if she found out you were talking on the down low, she’d freak out. Trust me that even if she said she was ok with it, even by asking her, you’d be permanently damaging your friendship, as countless thoughts will run through her head.

It’s only been a few months since she broke up, and you’ve been talking to him the entire time? She may think that you were the very reason the relationship ended in the first place. The fact that you’ve been keeping it a secret from her feeds even more into this line of thinking. If not that, why would you be talking to this guy on an intimate level when you should be spending time trying to help your best friend feel better? Any way you slice it, your position comes off as one of pretty major betrayal, and I can’t think this guy is so amazing that you’d risk a friendship over him.

Just reverse the tables and consider this situation: you’re hanging out with some friends and your BEST friend walks in with your long-term ex you recently split with. They sit on the couch and are getting all cuddly and cute. How much longer do you stay at that party, and how quickly do you find a new best friend?

Bottom line: long-term exes are off limits between best friends. No ifs, ands or buts. Go find yourself a new guy, and stop doing things behind the back of the person you claim is your best friend.

Best of luck!


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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Posted in: Ask A Guy, Love Advice
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  • SlimPhat49

    What the hell real friends dont date thier friends boyfriend unless yall doing a threesome

  • Saeryen

    I don’t like this…

    This whole “don’t date anyone who has ever dated your friend” thing could stop people from meeting the right person. Yes, you shouldn’t jump in right away because that’s hurtful, but if everyone involved is a decent person who would do their best not to hurt anyone else, you have a good chance that something like this wouldn’t break a friendship. Saying that girls would ALWAYS become enemies because of a transfer of a guy’s affections promotes hate between women. We need to promote love and understanding, and that falling in and out of love strengthens bonds. It doesn’t break them.

    It should also be noted that this attitude promotes fictional shipping wars and fanfiction in which girls are villainized for being the former girlfriend.