Dear Fuck-Up: How Do I Tell My Partner I've Slept With Lots of My Friends

Is this a fifth date conversation?

Two women and one man sitting on a couch eating pizza and partying.
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Ask A Fuck-Up
Ask A Fuck Up

Dear Fuck-Up,

Let me start this request with an unusual admission for an advice column: I am in a happy and committed long-term relationship with zero fault lines or niggling concerns.

Thing is though, I have a problem that has come up in most of my serious relationships, this one included, owing to the fact that I’ve had casual sex with a lot of my friends over the years. Usually it happened on a drunken lark when neither of us had anyone else to go home with that night, and because the sex was always pretty minor compared to our friendship, we almost always stayed friends after we decided to stop hooking up.

The problem is: there doesn’t seem to be a good time to tell a significant other that you’ve slept with a friend. Right away feels aggressive — you’re on your fourth or fifth date and meet up with a group of your people after, and you have to casually slip in “oh by the way, I slept with them a few years ago and *them* in July, but it was no big deal” — but waiting a couple months or even not telling them at all feels like you have something to hide, like maybe you *~caught feelings~* or are an untrustworthy partner (I didn’t and I’m not).

So what do you do? How and when do you tell your boyfriend or girlfriend that you and (quite) a few of your friends have fucked?


Friend Haver

Dear Friend,

Thank you so much for this much needed reprieve. Most of the letters in my inbox these days are from people with actual, depressing, difficult problems so it was truly a delight to receive one which amount to: I am constantly having sex with everyone in my life and it results in zero negative consequences for anyone involved, really. Just fucking when we want to, until we don’t any longer, and then retaining the ability to grab a drink together with basically no awkwardness or hurt feelings. By the way, in addition to this I also have a wonderful long-term relationship. Please help me.

I wouldn’t worry that telling your partner about these escapades would sound like you had something to hide, I’d worry it would sound like you were bragging. Which it probably will if you present this as a discrete conversation — something you Need To Talk About — or as some kind of breathless disclosure.

Surely, over the course of a serious relationship, natural opportunities to discuss your sexual histories present themselves. And if you are old enough to have fucked your way through a whole housewarming party’s worth of friends and acquaintances, your partner is old enough to understand that he or she will invariably wind up meeting some people you have woken up next to in the morning. Unless you’re devoutly religious, this is simply what happens when you date other grown ups. I mean, Friend, do you know any lesbians?? They navigate this shit constantly. It mostly turns out fine.

The one exception I would make to the “wait for it to come up in conversation rule” is if you are close enough friends with a former lover that you may end up say, having one-on-one dinners with them and your new partner. In that case, a casual mention is probably warranted. Something along the lines of, “we hooked up a few times years ago and it was very obvious that we were meant to be just friends.”

Other than that, I don’t actually believe we all have a solemn duty to give an exhaustive accounting of our roster of sexual partners to everyone we date. Congrats on all the sex.


A Fuck-Up

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