How to Do It

My Husband Watched Me Have Sex With My Best Friend, and That … Didn’t Turn Out So Well

A man and woman next to each other, and some lingers in front of them.
Photo illustration by Slate. Photo by Nathan Dumlao/Unsplash.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Every week, the crew responds to a bonus question in chat form.

Dear How to Do It,

My husband and I have been together two years, and only married three months. I’m 28 and he’s 47. About a year ago, I had sex with my best friend in front of him. I told him I wasn’t comfortable with him touching her, and now I do see that as selfish. It made insecurities arise in him, because he thought I enjoyed her more than him. Fast forward to now, and we’ve fallen bored with one another. We love one another very much, but as with many couples, we’ve just become complacent with sex. I’m bi, and we’ve been talking about another threesome, but with him having sex with the girl and myself (not my best friend this time). I struggled with the idea of the other girl feeling better than I do, or being better than I am. I got past that I suppose, but now I’m concerned what will happen after—if he will want another woman again. I don’t want our marriage and sex life to become all about threesomes. I do have my own insecurities, but I feel as if I owe him this, and honestly, I want it as well. I just need advice. The only threesome he’s had is the one we had in the past.

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—Three’s Company

Stoya: I’m worried for this writer. Two years, and they’re bored with each other? And she “owes” him?

Rich: That does seem like a short period of time for disinterest to set in. But if that’s the case, it seems fully reasonable to lean into the threesomes? Why not spice up their life? If they’re bored of each other anyway, why not have your sex life become all about threesomes if that’s what you’re both into?

Stoya: But ”I feel as if I owe him this”—are we sure she’s that into it? She says she is in the next line, but I’m not convinced.

Rich: I see that—hard to say whether her ambivalence is just that, or an inability to name the side she’s on.

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Stoya: I’m not sure her boundary around her partner not having sex with her friend is selfish, either.

Rich: Regardless, there’s nothing wrong with that boundary. Moving at your own pace means taking an internal inventory and asking your partner to respect it. It’s selfish only in the way that any honoring of one’s own needs and limits is.

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Stoya: So let’s say she is as into threesomes as he hopes she is. How does she deal with feelings of insecurity?

Rich: I guess you have to weigh them against the pleasure that pushing past them can provide. A lot of sex comes with insecurity. A lot of socializing comes with insecurity. Any situation that requires you to make yourself vulnerable can stoke insecurity. I think the key is to make overcoming it worth it. One way to overcome it is to realize that we tend to be our own biggest naysayers. So much insecurity ultimately amounts to anxiety, the fear of something that isn’t actually so, at least not yet.

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Stoya: Something that helps me with anxiety is imagining through to the most absurd possible outcome. So, what happens if he likes the other woman better? Does he pack his belongings into her vagina and carry her off like luggage? While whistling a song about rejection?

Rich: lol. It’s also important to keep in mind how attractive novelty is to people. So he might show signs of really enjoying having sex with a new person precisely because she is new. That’s one thing you can’t be as a partner, and so it’s unfair to yourself to compare. Novelty is too formidable of an opponent. I think to cope with this, understand that sexual excitement is fleeting (as their growing bored with each other attests), but she has this guy’s heart and can hold onto it.

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Stoya: I want to applaud the prudent choice to have sex with people who aren’t their best friend moving forward.

Rich: Yes. I think the letter writer here should talk to her husband, be upfront about her worries, and set clear mutual boundaries if they decide to move forward with the threesome. The conversation would also be a good time to discuss what they want, or what might be missing, from their own one-on-one sex. Our regular rec Mating in Captivity might help her frame that.

More How to Do It

I recently reconnected with a cousin who I hadn’t seen in about 15 years at a family wedding. He’s in his early 20s, I’m in my early 30s. When we saw each other, I honestly didn’t recognize him. He’s become quite a good-looking man, and I have to admit I was checking him out before I realized he was my cousin. My now-strapping cousin immediately glommed on to me at the wedding and told me how much he appreciated the time we spent together as a kid. It seemed innocent, but as he drank more throughout the night, he got increasingly physical and flirty, to the point where others commented on it. Toward the end of the night, he said he was questioning his sexuality and asked if he could come home with me to “talk about it.” He was very drunk, and I told him to go to bed. The next morning, he started texting me and asking to have a drink and talk more. I want to support him, but if I’m honest I am attracted to him, and I think he is to me, and …

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