My Best Friend Gave Me a Startling Proposition. I’m Inclined to Say Yes.

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 best friend “Ryan” thinks his wife is cheating on him with other guys. Yesterday, he approached me with a request that blew me away.

He wants me to try and get her to sleep with me. He says to let her go as far as she wants, even if it means we end up having sex.

Ordinarily, I wouldn’t even consider this, but I’ve known them since college. I always wanted to get his girlfriend in bed, but I had a girlfriend at the time, and by the time we broke up, the two of them were together. Should I tell Ryan to ask someone else to help him out, or would it be worth it for the chance to be with a woman I’ve been fantasizing about for years?

—Throw Caution to the Wind?

Rich Juzwiak: I would like to know more about Ryan. The fact that he says that the parameters of this possible arrangement are to let her go as far as she wants, even if it means they end up having sex, suggests that this is more than just a “Is my wife cheating on me?” trap. It seems like a cuckold kind of situation, something adjacent to it. So I think it would be better for everyone if everything were more explicitly stated. This is delicate, if not dangerous, territory they’re headed into.

Jessica Stoya: Generally, we assume that these letters are written in good faith. Even with that assumption, this whole situation is so dramatic that I think we do have to be a little suspicious. So, are we sure that it’s not that Ryan thinks his friend is pining after his wife and has arranged this as a test of the letter writer himself? None of this would be reasonable behavior, of course. Ryan is not reasonable, the wife is probably not reasonable, and the two options the letter writer presents are also not reasonable. But I would encourage the letter writer to question whether this test is meant for them.

Rich: Right, because if it is as straightforward as Ryan is presenting it, and his wife is doing something wrong, then asking his friend to engage in the cheating is probably only going to end up in drama and upset. I don’t see how you go through that situation and everybody comes out happy. It’s like, oh, there’s this mess happening in my life. Could you just go in with a leaf blower, scatter it all over the place, and make it 10 times worse since you’re my friend? If there is a shred of reality to this, I feel there has to be something more afoot. The way to combat negative feelings about your wife having sex with other people is not to get your wife to have sex with your best friend. That won’t work, and if that really is the scenario, that’s a mess. LW, don’t get your hands dirty.

Jessica: Emotions are inherently difficult; they are visceral and often uncomfortable experiences. So it is common and understandable that a person who feels hurt by suspicion that their spouse is cheating on them might come up with some hare-brained scheme. Also, I can see how shame and fear of rejection in the cucking version of this might lead to this sort of farce, but the least combustible response to any of these scenarios is to say, “Ryan, as a friend, I feel like something is not functional here. Let’s have more of a conversation.”

Rich: Also, I think that the more straightforward way of going about this would be to not do it in a way that deceives the wife into cheating, even if that’s what she’s doing. It would be to incorporate other people ethically. If you want to actually go there, don’t address everything that’s come before it. Just use this as an opportunity for a new chapter of openness. You could revise your life that way. It’s probably not the best method to just kind of pave over the issues they’re having in their marriage and start a new chapter, but it’s a way of doing it. It’s a much cleaner way of doing it, I think, than: let’s do this thing and trap her, and then you will all have already had sex, and then we’ll get to whatever resolution will come from that.

Jessica: The whole scenario feels like it came from a night of binge-watching detective agency reality TV shows.

Rich: It seems like it could also be the plot of an 80s porn that just didn’t quite stick the landing of figuring out everything logistically, but it’s hot enough that it will work on screen without you having to think about it too much. If you’re going to plot your life like this in such a deliberate way, pick a better plot because this one’s just too messy.

Jessica: I’ve had an atypical life, which has led me to many strange situations. And when I find myself feeling like I am in a CW Network teen soap opera, that lets me know that the least chaotic option is to slow down and try to consider all of the different possibilities and factors.

That said, some people truly enjoy drama, mess, and chaos. So if our writer is one of those people, go ahead and throw caution to the wind. But understand that in a couple of weeks, you’ll have made Ryan really sad and angry, and who knows what other unpredictable outcomes will occur. You make your choices.

Rich: Absolutely. And again, this is a best friend here, which doesn’t seem like a relationship worth risking. That’s not something that you can pick up that easily, but you know what you could pick up easily? Somebody hot to have sex with—more easily, at least, than a best friend. I don’t really get putting everything on the line for one encounter, and probably part of that is because I live in New York City, I’m a gay man, and just the opportunities are literally endless. 24 hours a day, you can have sex, if not hot sex with a hot person. So that’s my bias.

But I still think that for a lot of people, this is not something completely precious. This is not a scenario where the letter writer is like: “I’m a virgin, and I’ve never had a chance like this before, and my best friend has given me the one chance I’m ever going to have to have sex. Should I do this?” This is somebody we can assume has an active or average sex life. Just find somebody else. Give it a few weeks, you’ll come across them. Go to a sex club. There are opportunities out there.

Jessica: So for most people, it probably won’t be worth it. And if Ryan is really your best friend, don’t encourage this plot. Sit him down and ask him if he needs to talk.

Rich: Right. During that talk, consider dissuading him from entrapping his wife, which could only make a bad situation worse. The honesty and directness that you extend to Ryan should serve as a model for how he himself should move forward.

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