How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.com. Nothing’s too small (or big).

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

Dear How to Do It,

I never thought I’d be in this position. I am married and love my wife (30s). A gorgeous woman at work who works in a separate department (same office building) struck up a conversation with me one day at an after-work event, and she later added me on social media. I posted a photo one day and she replied flirtatiously in DMs, but she is also married and I didn’t think anything of it. She kept it up, and I barely responded, but then yesterday, she straight-up propositioned me for sex. No strings: a safe, one-time thing. I am an average guy, and women haven’t come on to me like this since I was in better shape in my late teens and early 20s. I don’t think I’ll get this opportunity again while I’m still young, and I don’t want to give it up. I know my wife would never give me a pass, 100 percent, but we barely have sex anymore post-kids. Is there any way I could do this, be happy it happened, and then move on, or am I kidding myself?

—Dirty Work

Stoya: The short version is yes, he’s kidding himself.

Rich: He’s asking us for a pass to cheat.

Stoya: And he’ll get no pass from me.

Rich: I’m against cheating in every scenario. Because of the lying it requires. I’m pro-nonmonogamy for the lying it helps circumvent.

Stoya: Exactly. It’s 2019. You can have a conversation about opening things up.

He can tell himself that he didn’t necessarily miss much, and gosh, wasn’t it nice to be asked?

Rich: This is their jumping-off point.

Stoya: You might not get the response you want—he seems certain he won’t—but you can have that talk.

Rich: At least it plants the seed. She’s not going to give him a pass, but she can understand why it would be useful for him, why this matters.

Stoya: It isn’t necessarily going to be an easy conversation, but it’s almost guaranteed to be easier than “I cheated on you.”

Rich: Yes, and though it may shock her, she might eventually appreciate this as an admission that he didn’t cheat but that the temptation was real.

Stoya: And how does he know she won’t give him that pass? It doesn’t seem like he’s given her the opportunity to give it or not.

Rich: I assume they’ve had some sort of abstract conversations about it, but yeah, nothing real and with actual stakes. We get so many letters where spouses (of all genders) are absolutely certain they could never bring up this possibility, and it makes me worry about the foundation of trust and honesty in their relationships.

Anyway, it often happens that the most exciting part of these scenarios is the flattery implicit in being asked. He should focus on that. He may have already experienced the highlight of the tryst that absolutely should not take place. The sex part might be fun in the moment, but almost certainly the ensuing guilt would outweigh the pleasure.

Stoya: In case he’s forgotten, first time hookups can be clumsy and awkward.

Rich: Who knows if they’re even compatible? He’s jumping at the first taker because she showed up (albeit gorgeously, according to him).

Stoya: He does seem rather flattery-driven, doesn’t he? And very fear-of-missing-out with “I don’t think I’ll get this opportunity again.”

Rich: Which doesn’t really seem supported by much. This is largely about his ego, I think, and if that’s the case, he should let the initial offer do its job.

Stoya: So he can tell himself that he didn’t necessarily miss much, and gosh, wasn’t it nice to be asked?

Rich: Yes.

Stoya: Or talk with his wife.

Rich: Or take it as an opportunity to build on that self-confidence, however he wants to do it. There’s a bittersweetness here, a looking-back at the good old days when women came on to him. He’s in his 30s. Hot dads are very chic right now. Lean into that.

Stoya: So, the silver lining is the strut he can exhibit based on hot daditude, confirmed by this semi–co-worker.

Rich: Yeah. And I don’t know, the implication is he isn’t taking care of his body like he once did. If it makes him feel that good, maybe he should get back to that in some way. I feel like I’m always telling people to exercise in this column, but it makes you feel good! It honestly makes me see myself differently regardless of the objective goods.

Stoya: And it might encourage his wife’s interest, and he does seem to be complaining about that somewhat.

Rich: The subtext is: This will not be the first time this comes up. He’s going to have some frustrating times with the situation as is. It’s not tenable, not if he’s taking a random offer like this so seriously.

Stoya: Yes, certainly not if he’s thinking of cheating.

Rich: They’re only in their 30s. Imagine yearning for sex for 50 more years.

Stoya: Oof. That sounds terrible. And to think, he could spare himself this fate by taking steps to change it. How’s that for motivation?

Rich: I think it will be really important for him to reaffirm his love for and attraction to his wife. As much evidence as there is out there that desire for other people is not a reflection of being dissatisfied with your partner, this is still a big concept for people to wrap their heads around. It’ll be really important to be careful and articulate.

Stoya: And to pick a time when they aren’t generally stressed and there aren’t likely to be interruptions, which can be difficult with kids.

Rich: None of this is going to be particularly easy, but that’s hardly a good excuse to not do it. This could be a moment of reaffirming intimacy with his wife—it seems very possible she misses it too. Or maybe she will be open to him having a discreet encounter. Best possible scenario: This solicitation from a co-worker turns out to be constructive. It’s in his best interest to keep it from being destructive.

More How to Do It

I’m a lady in my mid-30s, and over the past year, I’ve gotten close to a 40-ish married man whom I met through a work colleague. We’ve started an online-only sexual relationship, with plans to connect physically in the future. I’ve tried to cover my own electronic tracks—it would be quite devastating for my work life if my colleague found out that I was sleeping with her neighbor—so I’m not afraid of his wife tracing sexts back to me. For a variety of other reasons, this sexual relationship appeals to me at the moment. I don’t believe it will be long term, and it’s quite hot. I also know he’s had other relationships outside his marriage. We’ve had conversations about discretion, including from my co-worker, but I’ve never explicitly asked what his wife knows or doesn’t. Should I, or is that his business? I can’t decide if it matters, and I only worry if it would get back to my colleague.