Should I Tell My Boyfriend The Truth About My Exes?

Q: I’ve hosted a few parties, and some of my exes have come in attendance with their current girlfriends or situationships. My boyfriend has met them, but I haven’t told him about my past with these people. I feel guilty, but early in our relationship, we made an agreement to not tell each other about our previous romantic “flings.”

It’s weird seeing an ex shake hands with my boyfriend knowing that only one of them has the full picture. When my partner asks how we know each other, I can’t help but feel like I’m withholding important context. Should I tell him the truth if we’re going to see these people regularly? Or is it best left unsaid?

A: It depends on how you think he’ll react, and why you made this agreement in the first place. Because you both think the past is the past and therefore no big deal? Or is it because jealousy issues abound? Has one of you had a similar conversation go poorly before? If you and your partner agreed to not talk about “flings,” does that also include long-term exes? Because those might be in a different category — potentially more worthy of a discussion.

Also, I think it’s worth interrogating why you feel guilty and why you have the urge to tell him. There is no need to feel bad about having dated or hooked up with other people. And even though it can feel a little rotten, no need to beat yourself up if you occasionally feel a twinge of nostalgic longing for an ex. That’s normal. You’re doing amazing, sweetie. I promise.

Personally, I don’t necessarily want to know about every single person my boyfriend has ever hooked up with — not my business, not my problem. But if I’m frequently crossing paths and interacting with a serious ex, I feel like a heads up would be good. Not because of envy or concern that he still might be into her, but simply because it’s kind of awkward to not know! Especially if I’m the only one in the dark.

That said, neither my boyfriend nor I get particularly jealous, angry, or emotionally volatile, so it’s very easy for me to trust that these interactions would go well. But that’s not the case for everyone.

Here’s how a few different scenarios could play out.

If You Tell Him...

Your partner might get mad.

If you have a hunch he won’t handle the news well — by being sullen and moody all night, not supporting you throwing parties or hanging out with friends, questioning your actions and motives — then I would absolutely skip telling him. You’ve already agreed to not talk about it, so please don’t feel guilty about holding back.

I would also think long and hard about being with a person like that. (OK, I wouldn’t think long or hard. I would dump his (a**). 

He might be a little bummed out.

If you feel like he’d be somewhere between aggressively upset and throwing a celebratory parade, I’d still probably avoid mentioning past hookups unless the situation arises. If, however, he asks how you two know each other, you can say, “Oh, we used to date a million years ago.” And then move on.

Later, check in with him — not right after the conversation, but at the end of the night or the next. morning. You might say something like, “I know we talked about not sharing info about our exes. Is that still the plan? I don’t want to feel like we’re withholding anything from each other.” Talk it out. You might re-evaluate the agreement, or find that out that he’s not remotely jealous.

If You Don’t Tell Him...

It might be NBD.

It sounds like you’re on at least somewhat friendly terms with your exes, and maybe he is too. If you get the vibe that he’d be fine with a heads up, before the party you could say, “Hey, I know you don’t want details about the past, but I feel weird being cagey about how I know certain people.” Then take it from there.

It’s fine — healthy, even — to let behavior and boundaries evolve as your relationship deepens. It might be nerve-wracking in the moment, but it’s a beautiful thing.

Sometimes not sharing information isn’t about hiding a sordid truth, but rather understanding that the information is not necessarily helpful to your partner. Even if your guy isn’t a possessive weirdo, and even if your ex is not The One Who Got Away, sometimes unwanted info is upsetting.

Also?

A kind omission is not something you should punish yourself for, especially when you’re sticking to the agreement you already made.

On the other hand, giving your boyfriend a heads up that you and some other guy used to dry-hump in college might make things less awkward. (Maybe don’t actually use that word.) You probably don’t want your partner to be hurt by this information if someone offhandedly mentions it in front of him. That is way more likely to happen if you two keep the agreement that nothing be shared.

There’s no one-size-fits-all answer here. Do your best to consider which situation you’re in, how your partner might react, and what the spirit of the initial agreement was.

Would this information make your relationship better or easier? Or is it irrelevant gossip that would just sting? You don’t deserve to feel guilty about having had previous relationships (however casusal), nor should you feel the need to keep uncomfortable secrets. Either way, it’s time to let your partner in or let yourself off the hook.