How to Do It

I Just Met My Casual Fling’s Husband. Oh God.

She thinks he won’t care “that much.”

Man holding a shoulder bag and a book. A shushing emoji floats around him.
Photo illustration by Slate. Photo by Ben White on Unsplash.

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

Dear How to Do It,

A few months ago, I was temporarily transferred to a new city for work. Shortly after arriving, I met a woman at a bar and we started hooking up. She told me she was in an open marriage and was just interested in a casual fling, which was fine with me since I knew I’d only be here temporarily. She’s great. The sex is amazing. The conversation is everything from intellectually stimulating to silly and fun. We’ve even had a couple of weekends away that were wonderful and made me forget she was married. I know that we will never be anything more than what we are, and I am fine with that. However, recently I went to a company event and saw her there…

She was there with my boss, who is her husband. Rick is the head of the company branch where I am working and is technically my boss’s boss, but is still very high up in the company and could have me fired.

When introduced, we acted like we didn’t know each other, but I was freaking out and left early. When I talked to her later—still freaking out—she told me it wasn’t a big deal and Rick wouldn’t find out. And even if he did, it’s not like he would care that much, especially since we don’t work with one another every day. I might see him once a month for a monthly meeting or when he comes to the office to see my boss. I only have four more months here before I move on, and I’d like to not end things with her, but I am still freaking out that she is my boss’s wife. Should I end things? Should I trust that Rick won’t care if he does find out?

Rich: There is a special strain of How to Do It questions that just reads like a low-budget indie movie. These kinds of titillating, morally ambiguous, open-ended mini-essays that make you wonder, “Where could this go?” Could go anywhere! If I were a screenwriter, I’d be mining these questions for that. I don’t know if you saw the one that I answered about the woman whose husband was having an affair and the PI kept reporting the information and she just became so obsessed with this that she didn’t want them to break up.

Stoya: I was thinking this one would make a great porn script, but what would happen is you see the writer and the woman, and then Rick does find out, but rather than fire the guy— because I don’t think there’s an HR person in the world that would know how to wrap their heads around this particular situation—Rick sends his own lover because of course the—

Rich: Oh, perfect.

Stoya: The inappropriateness escalates,

Rich: Yes.

Stoya: Throughout the porn plot.

Rich: Yes.

Stoya: Sends his own lover, who’s a very attractive woman who also works at the company to dominate our writer, and he finds a very special part of his sexuality that was unbeknownst to him thus far. And then I don’t actually know, I guess the third scene is Rick fucking his wife. And then in the fourth, it turns into an orgy.

Rich: Of course.

Stoya: And everything’s out in the open.

Rich: Yes. I was definitely seeing an orgy as soon as you started setting that up.

Stoya: Life is not a porno and this has a significant  chance of blowing up in our writer’s face.

Rich: It’s true. If this woman is capable of being intellectually stimulating and she seems generous, there is this self-assuredness to her that I would be at least open to interpreting as she knows what she’s doing. She’s so self-assured that it seems like she’s done this before or that this arrangement has been tested in the past. So there’s also the possibility that she’s dead-on: “Whatever. Who cares?”

Stoya: Yeah, the “wouldn’t care that much” line. That’s where most of my worry is coming from.

Rich: That makes sense.

Stoya: Because I’ve been in open relationships with people who do not mind at all.

Rich: Yeah.

Stoya: They are neutral or thrilled or whatever it is, and I would not describe them as, “wouldn’t care that much.” Whereas I’ve also been open with people who weren’t really comfortable with the situation, whether it was open relationships at all or the specific structure of what we were doing. And I have literally thought, “Oh, they won’t care that much.” And then it turns out they do care a lot.

Rich: I would say that I’m kind of in a situation of wouldn’t care that much. In general, the open aspect of my relationship is very smooth sailing, but we hit some patchy waters sometimes. Overall, non-monogamy hasn’t torpedoed anything. There’s never been a dramatic escalation involving anybody but the two of us. And it never usually even gets there. At worst, it’s a conversation that might be a little bit tense leading into it. So it’s true.

I mean, look, this woman could just be really, really reckless, but the profile doesn’t really seem to fit that exactly. It seems to me that if there were a reason to be concerned, she would be the one to be concerned. It’s her marriage. I mean, this guy is breezing in and out and it’s a job. It sucks to get fired from a job, but you can get a new job relatively easily with little emotional heartbreak at a certain corporate level. The marriage torpedoing is a far bigger deal. She doesn’t seem pressed about that. It seems like maybe you want to play this more carefully than just conforming to my assumptions.

Stoya: No, I want to present the writer with the spectrum of possibilities. And then tell them to gather more information to help them discern which of these possibilities is most likely. And then do a gut check on how comfortable with gambling they are—

Rich: Yes.

Stoya: In general and in this specific situation. How do you not ask “Where do you work?” And I have absolutely accidentally had sex with someone close to someone I’m also having sex with.

Rich: Right.

Stoya: But not in situations where it is so easy to through the course of casual conversation, “Oh, you just moved here for work. What company?” “Oh, yeah, my husband works at that company.”

Rich: Or even more basic than that: “What do you do?” “Oh, that’s interesting. My husband is also in that line of work.” “Oh really? Where does he work?” You know what I mean? That’s a very logical kind of progression to have.

Stoya: Yeah. When it’s something more scattered and loose like the entertainment industry, or you both work in tech but on different coasts and it turns out you know each other and can’t stand each other, that’s a little harder to spot than people who work in the same industry, in the same city. So that makes me question how experienced and elegant she is with these things.

Rich: Yes. Regarding the HR thing, I wonder how much actual concern is worth having. I suppose people in power can find excuses to fire people at their will. Sometimes they can figure out a way. I don’t know that this is a fireable offense, necessarily?

Stoya: Regardless of the rules, bigotry or even discomfort can weigh the way an issue is evaluated… So let’s say hypothetically Rick is like, ah, you’re banging my wife, I’m going to get you fired. And then HR is like, what’s going on here? And Rick says, this guy is banging my wife. And then HR decides they’re not even going to ask about open relationship structures. Or, they think oh, it turns out that you’re all open and that gives me squicky feelings on the inside. So this guy gets fired and Rick is going to have trouble in the future. That’s not a super likely outcome—I don’t feel that’s anything close to inevitable, but it is a possible path that this goes. And then he’s left trying to explain.

Rich: Right.

Stoya: But if he took a gig and then does get fired a couple of months early, that’s probably not a thing that’s going to be noticed and questioned on a resume at an interview for the next gig. Lots of people have a couple of months gap between leaving one gig and finding another. But if it’s all the same company with offices in different locations, then the social perception of the whole office is something to consider.

Rich: Basically the question is: What would be more detrimental, to lose your fuck buddy that you have great chemistry with or your job? What is easier to attain? What’s easier to get more of? In my experience, I could find another sex partner that I connect with very well, pretty easily. I live in New York, I’m a gay man. They’re out there. A job’s a little bit more difficult, especially in media. I think that ultimately that might be the calculus. That might be what you need to weigh.

Stoya: Yeah, gather some more data, weigh your options, and maybe make a chart. It’s a lot of different things to consider all at once.

Rich: Pros and cons in their respective columns.

Stoya: Good luck.

More Advice From Slate

My wife and I have been in an open marriage for five years. For as long as I have known her, my wife has been interested in “incest” role play. While it isn’t my cup of tea exactly, I have been willing and happy to support her in her exploration of this kind of fantasy and role-play. Recently, though, things have started to move in an uncomfortable direction for me.