My Boyfriend Won’t Shut Up About Sex With His Ex

Q: My (21M) boyfriend (20M) is best friends with his ex; she’s even spent the night at his house from time to time. Recently, their conversations have shifted into a more sexual nature, including going into detail about their life as a couple. Honestly, I’m extremely uncomfortable with them being this close.

I’ve been imagining them together in my head and I’m struggling to think of anything else. It’s consuming me. I already struggle with the fact he’s been with others and it eats at me, but to have someone explain what they did in such vivid detail has turned my issues up to 100. I don’t know how to proceed with anything. It’s even affecting our sex life because I start to think about it and just break down. What can I do?

We’re all human and this is our first time being alive. So I am leaving the door a tiny crack open to the possibility that your boyfriend is simply a dipsh*t who doesn’t know what he’s doing.

A: In general, it’s a green flag when someone is friendly with their ex. It usually means they made mature and kind decisions at a difficult time (a breakup). I am not against a partner hanging out with an ex — even one on one! Ultimately, either you trust them or you don’t.

That said! That! Said! My dude, this is not “friendly with an ex.” This isn’t even “friends with an ex.” This is some weird other thing that we don’t have words for. It’s messy. It’s immature. And more damning than all of that, it is cruel to you and harmful to your relationship. I do not know where your boyfriend got the sheer boldness to act this way.

My first inclination was to tell you to break up with him. Life is long (longest thing you’ll ever do), and your 20s are a great time to figure out what you do and don’t want in a relationship. Now you know: Thoughtless behavior is not for you.

It’s also a time when things should be relatively easy. I’m not saying that there aren’t important talks or lots of pain or big heartbreaks. I just mean that when you are in a relationship with someone at that age, it shouldn’t be an uphill battle. Please save that for when you’re 47 and your apartment floods and you’re caring for your mother-in-law because you lost your job and are at home all day and your kids won’t stop fighting in the hotel you have to live in for a month and your partner is not helping. Or something else dire and exhausting.

From the outside — the place where it’s easy to say stuff like this — this relationship simply does not seem worth it. Frankly, who has to be told that recounting the positions your ex used to achieve in the back of your Ford Fiesta is in poor taste? That is fairly basic! And what is he even getting out of reliving this stuff, in front of you or otherwise?

There are already too many ways the world can hurt you. You don’t need to add this to the list.

Now! All that said, I like to leave room for people to Mess Up Big Time. Mostly because I’ve MUBT (and probably will again), and support those who have, too. Also because, you know, we’re all human and this is our first time being alive. So I am leaving the door a tiny crack open to the possibility that your boyfriend is simply a dipsh*t who doesn’t know what he’s doing.

If you feel like he’s acting out of a lack of self-awareness rather than out of ill intent, or if you’ve never discussed how painful this situation is for you, then you might try to have One Big Talk.

There are many relationship problems that require Multiple Big Talks. This is a rare case where one will do! I would say, “Hey, I don’t need you to stop being friends with your ex, but you talking about the sex you used to have — either with her or with me — is not OK. It’s weird and mean to me and I’m not sure what you get out of it. It’s making me insecure and doubtful, and I don’t think you want me to feel that way. So stop.”

I’m usually very against asking partners to cut people out of their lives. It’s often bred from a misplaced sense of jealousy, and can be a form of abuse rather than a mature response to a situation. However! If you’d like him to step away from her, either temporarily or forever, that seems very reasonable here. You are not asking for a lot.

There is no room for négociation (which is French for negotiation). None at all. You do not need to compromise or make him feel better for having hurt your feelings repeatedly. If he wants to be good to you — the base-level requirement for a boyfriend! — he will respond with horror at his actions and enthusiasm for changing. Anything other than that is ludicrous.

There are already too many ways the world can hurt you. You don’t need to add this to the list. Here is my sincerest directive: Pick people who find it easy to treat you well.

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