Your Bestie Slept With Your ‘Friend With Benefits’? Girl, Please

Demetria Lucas D’Oyley
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Dear Demetria:

My best friend of seven years slept with my “friend with benefits.” Yes, I have no claim to the man, but I let them both know prior to this incident—after they made out in front of me while drunk—that it made me uncomfortable. They both agreed to respect how I felt.


Fast-forward two weeks: We all go out and have a couple drinks. Everyone crashes at my place. We wake up the next morning and she tells me they had sex in my house, on my couch, while I, other friends and my younger brother were sleeping not 50 feet away. I'm disgusted with both of them. How do I go about dealing with them? I feel like they both, mostly her, completely took advantage of my trust. —Anonymous

Um … what?

There is so much—so, so much—going on here that I don’t understand. It really seems as if you’re leaving out some critical details about lifestyle choices or sexuality that would make this story more cohesive.

Beating around the bush isn’t my strong suit, so let me just ask: Did you and your bestie of seven years ever have a threesome with your “friend with benefits,” or perhaps with other men prior to him? That is the only way this story even sort of makes sense.

If you and your friend are used to having threesomes or sharing guys in some fashion—just FYI, you wouldn’t be the first person to write in about it—then there would be a somewhat logical explanation for why she would make out with a guy you’re dating—or just having sex with—right in front of you. Her thought process would be something like, “We always share! So this is perfectly fine!”


Maybe she was warming him up for you and didn’t think she was out of line. That still wouldn’t explain why she had sex with him when you were sleeping just a few feet away and after you asked them not to, but I’ll get to that in a minute.

This, or something along these lines, has to be what’s at play. Because anybody else would have gone full HAM if she found her best friend and a guy she was having sex with making out. The general rule is that a best friend shouldn’t be kissing (or flirting with)—much less sleeping with—a man you’re dating unless she has permission. (Hey, some people get down like that.) It doesn’t matter if you don’t have a committed relationship with the guy and you’re both single.


I mean, it’s bold to go after your best friend’s sex buddy, period. But it’s huevos almighty to do it right up in front of your face, like, “Oh, I see you sitting there and I will pretend I don’t.”

Then you see this profound disrespect and you just say, “Hey, guys, don’t do that anymore”? I’m not saying you should have flipped tables. I am saying that no one would blame you if you did. I’m also saying that at the very moment you saw them making out, you should have ended your friendship and your sexual relationship, on the spot. That’s what most people would have done.


You chose not to, for whatever reason 99 percent of people will not understand. And 100 percent of people will never understand why you maintained both relationships and chose to go out drinking with them and then invited them home with you and didn’t sit up all night watching them. I’m extremely baffled by a lot in this story, but this part baffles me the most.

I’m not shocked that they had sex. I’m not shocked that she told you about it. It’s pretty clear to me that your friend has a long history of overstepping what most people would consider basic boundaries. She did this so, so freely and so, so messily and still has your friendship—even though this isn’t the first time she’s been extra. No one starts with making out with your guy in front of you; this indicates to me that your boundaries are way off-center, too, or have been in the past.


What your bestie did was a huge breach of trust. For whatever reason, you gave her a second shot after she made out with your guy, and she still slept with him even after you told her not to.

There’s only one reasonable reaction here: The bestie and the jump-off are cut off. Let them go have each other. Clearly, you’re no longer down for whatever situation existed in the past, and your best friend is still about that life. It’s time to find new friends and a new man who know how to respect your new boundaries.


Demetria Lucas D’Oyley is a contributing editor at The Root, a life coach and the author of Don’t Waste Your Pretty: The Go-to Guide for Making Smarter Decisions in Life & Love as well as A Belle in Brooklyn: The Go-to Girl for Advice on Living Your Best Single Life. She answers your dating and relationship questions on The Root each week. Feel free to ask anything at

Previously in Ask Demetria: “Spending His Birthday With His Boys Instead of Her Proves She’s an Option, Not a Priority

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