Social circles can start to feel pretty small when you start hooking up with a friend’s ex. Not gonna lie, this sitch is certainly hairy—it’s the sort of thing that if you’re not careful can ruin your friendship. There are, however, better ways to walk this tight rope. Here’s some advice to help a few different of varieties of this conundrum.
You hook up with/started dating a friend’s ex. Your temptation may be to simply not tell your friend what’s happening. What they don’t know can’t hurt them, right? Wrong. Chances are, this juicy tidbit will come out eventually and when it does, you’re going to look super shady for hiding it from your friend. The better option is to come clean right away and say, “I’m really nervous to tell you this because I care about you a lot and I don’t want to hurt your feelings or upset you. This is really awkward to talk about but….(explain the situation).” Let your friend know generally how it happened—but spare them the gory details.
You start dating an ex your friend still has feelings for. This is the trickiest situation of them all. It’s one thing to date a friend’s ex, and it’s another thing to do that when your friend is still pining over them. I would think hard here if it’s really worth it to you to date this person. Chances are, this will really break the trust of your friendship, and it could take a while—if ever—to earn that trust back. If you do decide to move forward with this relationship because you feel you have THAT strong of a connection with the ex, explain where you’re coming from to your friend. Although they will still likely be very hurt by it, knowing that you’ve really thought about this may help them feel better about your friendship. But keep in mind, your friend may decide that he or she can’t be friends with you anymore…and that’s a risk you have to take in this situation.
You start dating an ex who had a nasty break up with your friend. Break ups can really bring out the worst in people and make people say and do things they don’t really mean. But meant or not, those things can still hurt. If you’re dating an ex who had a brutal break up with your friend, you need to set a ground rule: your new sweetie shouldn’t bad-mouth your friend to you, and your friend shouldn’t bad-mouth your new SO to you either. Furthermore, your new partner shouldn’t be talking crap about your friend anyway. If they’re over the old relationship and ready to move on with you, then they need to be over ALL of it—including the hurt feelings. Very likely, your friend’s biggest concern in this situation is that you may turn against them. Anticipate that, and make clear that you want to stay completely out of whatever bitterness is between your friend and their ex. Tell your friend, “My opinion of you is not going to change. And, I’ve specifically told X that he/she should not say anything negative about you to me.”