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Do You Tell Your New Significant Other That You’ve Slept With Someone in Your Friend Group?

Pop quiz, hotshot: You meet someone new, and it’s time to introduce this person to your friend group. Trouble is, you hooked up with your “friend” Alicia three years ago in a hot tub on Cinco de Mayo. Do you tell your partner? Slow down, pony! It’s complicated.

Let’s start with what happens when you don’t. You could end up sounding like this joker who wrote into an advice column at the New York Times asking how to tell her fiancé — whom she’s been dating three years — that she fucked two of the dudes in her friend group and everyone knows but him. She wants to come clean and tell the truth in the interest of starting off their marriage right, but is understandably afraid he will be mad or feel like a sucker. “I’m not ashamed of what I did, but if I tell my fiancé, I’m afraid he’ll be hurt that I waited so long to tell him,” the advice-seeker writes.

She is correct. She shouldn’t be ashamed of what she did, and there’s a chance he won’t care, but not telling someone makes it seem like a deliberate omission that can look very similar to something we call a lie.

What to do?

This is really such a young person’s problem, because 20-somethings and college-aged people typically haven’t paired off yet, so they still hang out with all their friends from college or post-college. And that’s a weird mix of exes and hookups and actual friends and their partners and so on. It’s also normal at this age to date pretty incestuously within a friend group—at one point or another, everyone has at least had a crush on someone else in the group, or made out with them or slept with them.

The first mistake of this whole situation is that you also tend to think that you’re super sophisticated about it. Sure, maybe Alicia sometimes acts weird about the hot tub, but hey, you’re all sophisticated people and that’s just modern life!

But then you get a little older. You burn through dating options in the group, and now, you start dating outside the group — maybe someone you met at work. Here’s when you decide to make the second classic rookie mistake of bringing the outside person into this group to see if they mesh, only without telling them shit about any of the dynamics.

Trouble is, Alicia is in love with you, bro! She’s only been acting like your friend in the hopes that you’ll realize you fucked up and actually date her. This isn’t going to end well!

That’s because it always comes out that you used to fuck Alicia. Always. Here’s how:

Scenario #1: New Partner Asks You Directly If You Fucked Alicia

You introduce your partner to your friends, they have eyes and observable reality tells them that it’s a chummy mix of men and women, so eventually it occurs to them that maybe you fucked one or more of these people. It’s probably Alicia! Your new partner turns to you and is like, “So, did you and Alicia ever have a fling or anything romantic?”

Scenario #2: Alicia Acts Weird and/or Flirty

This is the one where your new partner looks around at your friends and picks up on the Alicia vibe. You know the vibe. The we-fucked-once vibe. Alicia is acting weird. Alicia is just a little too chummy. Alicia is outright flirty. Alicia makes a joke that seems too intimate, hinting at a more than friendly past. Or, more commonly, Alicia acts weirdly not friendly to your partner because Alicia still has feelings for you. Then your partner has to ask, “So did you and Alicia ever have a fling or anything romantic? Because she seems really into you/really mad at you/really weird toward me and I don’t even know her?”

Scenario #3: Some Other Total Moron in the Friend Group Makes a Reference to You Having Fucked Alicia

This is the one where someone in the friend group is a moron, or actually wants to stir up shit, and will outright refer to the fact that you fucked Alicia one time in a hot tub on Cinco de Mayo after you guys all did those Jell-O shots. OMG. You were all so hammered! Then your partner, now embarrassed and upset, has to turn to you and say, “Wow, so, you fucked Alicia in a hot tub on Cinco de Mayo after all those Jell-O shots. OMG. You were all so hammered! Thanks for telling me!!!!”

Again, your crime isn’t that you fucked Alicia in a hot tub, although they’re kinda trashy for sex. It’s that one of the basic tenets of consideration you give new partners is that you don’t send them blind into your weird stupid past without some intel and support, bare minimum. You don’t owe anyone your full sexual past, but c’mon, give someone a heads up if you have a weird past with someone you expect them to actually hang out with all the time.

Often, when your partner is about to meet that friend group, they will usually be like, “I’m excited to meet your friends, tell me a little about them first!” This is when you’re like, “Cool yeah, so Brad will be there. He works in aviation and is like, so good at keg stands. And then there’s Alicia, she’s like, well yeah, we kind of had a fling three years ago. But it was a one-time thing, and even though sometimes I get the feeling she still likes me, it’s one-sided, and we’re just friends. That’s way in the past. Mark will be there, he’s a cool guy — his girlfriend Sarah is funny…”

If that seems like a lot of words, it is. But these words may save your relationship. It’s the perfect prep so no one has to sweat weird vibes or get embarrassed. If you don’t do this, you end up three years from now like that joker up top. You’re about to marry someone, Alicia is going to be at your wedding, and your future wife has no idea you fucked her! That’s a cool memory for the photo album.

Speaking of that joker up top, in response to her, advice guru Cheryl Strayed reminds the advice seeker of her fourth mistake: By not telling the fiancé, she gave him no chance to decide if he wanted to be friends with dudes she slept with, which kind of should have been his choice:

Perhaps if you’d told your fiancé about your past with these men, he wouldn’t have wanted to become friends with them. Perhaps he wouldn’t have been fazed at all. You don’t know. You now have the opportunity to find out. It’ll likely be an uncomfortable conversation.

I don’t mean to imply here that such situations can’t turn out okay. Lots of people are friends with exes, bring new partners into the scenario and everyone gets along fine. But it happens because the relationship truly is in the past and no one is still scheming to get back together. More often than not, however, friend groups have strange dynamics when they include past hookups, and someone can be harboring feelings. That’s life and everything, but again, prepare someone you actually care about with some kind of heads up.

It’s always much easier to hide the truth. But if you do, and it turns out that your ex fling is a bit of a gargoyle, and you bring a new partner into the mix, they may very well try to sabotage it. It’s happened to many, many people I know, and it’s very awkward.

None of that will be as damaging, though, as you sabotaging it first by pretending it never happened.