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How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous!
Dear How to Do It,
My boyfriend and I recently talked about opening up to the occasional third in joining us for sex. The conversation was really fun itself; it felt like sharing a fantasy together, and we’re both excited about trying it out.
The problem is that over time I’ve come to realize that the reason for most of my lackluster sex before meeting him was that I’m more attracted to people and into sex if I have a good friendship going with the person before we go there. For example, my boyfriend and I were pretty good friends for about a year before either of us made a move. I’m just more comfortable, more myself, and more confident being flirty and in the mood with someone I already trust. I really envy my friends who can just turn on the charm for strangers.
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My boyfriend expressed that he didn’t want to have sex with any of our current friends because he said it would be awkward. He doesn’t mind sleeping with someone we’ve only briefly met. But is there a way to make this happen otherwise? Is there a way I can become more confident being this fun version of myself around new people? I would love to make this happen for us!
—Friends to Lovers (she/her)
Please keep questions short (<150 words), and don’t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.
Jessica Stoya: Why is there such a strong assumption that what our writer needs to do is change herself and her comfort level in various contexts in order to perform the behaviors of being the flirty, charming, and fun version of herself? That, for me, makes me go, whoa, whoa, whoa.
Rich Juzwiak: I do think that it’s natural to look around and say, “I’m seeing all these other people who are having this fun time that can bond with strangers very easily and have these fun sexual encounters. What’s wrong with me?” But maybe this is where labels become really useful because there are other people who feel similarly to the letter writer. It sounds something like demisexuality, where there needs to be an emotional connection before you can feel inspired to have sex.
That label is useful because it doesn’t have to feel like, “Oh my God, I’m so weird, what’s happening to me?” This is a phenomenon that so many other people have experienced that there is a name for it. And that might be what’s going on; in which case, how do demisexuals have casual sex? I think it’s, by definition, less casual in those cases with those people.
Jessica: I think it is worth spending some time with descriptions from demisexual people about how they experience desire, seeing if that resonates, and then considering what you just suggested. It’s also worth considering: Is there an inherent need for strong desire for rapport with a person before she feels desire? Is there a social awkwardness or general reservedness that just isn’t bubbly, fun, easygoing mode until she gets to know a person? How much of each is going on, and how might the two be interacting with each other? Because at least on the bubbly, fun mode front, women who are open to threesomes are still rare enough that you don’t necessarily need to exert yourself that hard, right?
To go ahead and bring the economics framework into it, even though that can get really dodgy really quickly, as a woman who’s willing to have a threesome, you’re high enough value—you don’t need fancy packaging.
But also, if the boyfriend doesn’t want to have a threesome with anyone that they have a closer relationship with than just having briefly met, and a big part of how she functions is needing a real relationship and rapport, unless he’s OK with her building that, which I’m going to assume is really unlikely, then this might not be a thing that you can make happen.
Rich: Right. I do wonder if there’s a middle ground they can meet. Say the writer isn’t necessarily fully demisexual, but she has these tendencies. Well, maybe you then cultivate a relationship with someone outside of your friend group that you think might be a good third. You can specifically do it for this purpose, but just keep in mind that in a more casual sex mindset, if you take too long, people move on a lot of the time. Also keep in mind that there’s no particular guarantee that this is actually leading somewhere, so then it’s like, “What are we doing? Now, I have a new friend that I might have sex with one day.” But if you could magically meet somebody who likes to go at that pace, then maybe it works out. I don’t know how practical it is, but there is a potential middle ground there.
Jessica: Also, talking through that possible middle ground is a really useful way of testing whether this might actually work. Because people in general will think it would be really fun and erotic to have threesomes or date a stripper, and then as soon as they’re in the reality of it and these fantasies involve real people, often a whole lot of jealousy, need for control, and all that kind of stuff boils over.
So, talk it through: What if the two of them looked for friends outside the friend group? What if she made friends and then, if they’re potentially interested in a threesome, introduced them to him, and his experience is having only briefly met them, and there’s not the awkwardness of being embedded in the social group? Considering what that might be like in detail can help make it feel a little more real and save everyone a big “Oh no” moment.
Rich: Yes. Or she just completely abandons what her intuition is telling her about herself and makes a conscious decision to say, “No, this is at odds with the kind of sexual experiences I want to have. Let me try this.” And then if you have a few bad threesomes, then you realize for sure, “OK, this really isn’t for me.” Then, somewhere down the line, perhaps you meet a friend outside of your friend group, and then one day magically you end up in bed, but that’s almost something you can’t orchestrate and can only hope for. You’re just not going to have it in every way in this scenario.
Jessica: Again, really, if a big part of the hang-up is “How do I force myself to be fun and appear relaxed with people I don’t know?” you don’t have to do that. You’re showing up as the gender that’s less interested in these practices. Your boyfriend can do a lot of the heavy lifting when it comes to the socializing and sealing the deal. Don’t sit there with your nose in your phone scrolling, but you can just be like, “I’m going to show up as I feel like showing up.” And if they’re interested in that, great. If they’re not, you’re not a sex robot. It’s not required to say, “I’m going to step past my comfort zone, put on a show of this aspect of my personality that does not feel genuine to express right now in order to participate in a threesome with a boyfriend who wants that from me and a third person who didn’t even get the chance to accept me as I am.”
Rich: And hopefully the exploration part of this is fun enough that even if you make a failed attempt, you’re like, “Well, that was an experience.” But if you are ultra-sensitive, then tread carefully and certainly do not push yourself into territory where you might leave feeling worse than you went in. Don’t scar yourself for a night of fun.
Jessica: Outside of all the sex stuff, think about what you really envy in your friends who can be super charming to strangers. Is that maybe a thing that’s more throughout all of life that you want to try to work on? But if that’s the case, a threesome with a boyfriend whose main boundary is, “I don’t want to know the thirds well,” might not be the most manageable context for figuring out how to be casually social.
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I was in a loveless (largely sexless) relationship for way too long. When I finally got out, my body had changed a lot: I’d had several kids, was older, and fatter. But even more than this, I think I just lived in my head for so long… I feel kind of disconnected from my body. I’ve always struggled with this a bit due to trauma/body dysmorphia (which is probably how I ended up in this unsatisfying relationship in the first place), but it’s way worse.