Ask A Guy: How To Successfully Date Your Ex’s Friend

Hey Joel,

So, my ex and I broke up a few months ago. I’ve been talking to his friend recently, and we’re thinking of dating. The breakup wasn’t contentious, and his friend wasn’t involved at all at the time, but I still feel kind of weird about it. Is there any good way to go about this?


I totally get why you feel a bit weird about things with this new guy, but I think if you go about this the right way, everyone should be cool with the situation. In reality, your new guy has a lot more work to do than you, but you should definitely make sure you’re on the same page first.

The reason you’re feeling weird about it is likely because it’s your ex’s friend, and since things didn’t end horribly between you and the first guy, you don’t want to hurt his feelings. Also, I am sure there’s a bit of “am I being shady” kicking around in the back of your head, but if you really did have a clean break and had nothing to do with your new guy, I wouldn’t stress on that any longer.

Insofar as the best way to go about trying to make things okay, I’d have your new guy talk to your old guy. As friends, they need to get things straight on a number of levels, as your ex may not be very happy about his pal’s new girl. Even if there was absolutely nothing going on between you and this new guy during your last relationship, it’s still tough to drop that idea on a friend.

To be honest, you don’t really owe your ex any sort of explanation. You broke up, you moved on–it’s that simple. In many ways, any problems with your ex will be between him and your new guy. While your ex may not want anything at all to do with you anymore, he really can’t be pissed that you’ve found someone new.

In the end, the sooner you handle this, the better. It will make things easier for you and your new guy, and if your new guy can’t bring himself to man-up to your ex, that might be a sign that he’s not the sort of guy you want to date.

Best wishes,


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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  • Logan

    So me and my ex boyfriend broke up almost a month ago and I’m still unsure of why we broke up. Everything was going great we started talking before at the beginning of the summer then he just stopped texting me but then at the beginning of this school year we started talking again and started dating. So he met my parents and we went to homecoming together everything went amazing!
    Two days after homecoming(a day before what would’ve been our 1 month anniversary) just out of no where he says he doesn’t think he needs a girlfriend right now because he’s going through a lot with school and his family. I didn’t believe it at first but after talking to him more I believed him. It still doesn’t make sense though because he acted like he was into me so much that it just doesn’t make sense how he can just change his mind just like that. We also work together and he doesn’t even act the same since we broken up. I admit I did something really stupid and put a note on his truck after I got off one night but that how we were, we were weird together it’s how our relationship was. I apologized later for it and he said it was totally fine.
    I just don’t know what to do because I really did like him and I think he still has feelings for me as well.