Longtime listener and reader here. Late-thirties gay man from a progressive city in a 1.5 year non-monogamous relationship with a really great guy. We're super compatible when it comes to socializing, entertainment, eating, music, art, politics, and all that fun stuff. The sex is great—adventurous, connected, comfortable, and a good balance of dirty/sweet. We've been non-monogamous for our entire relationship and have the occasional conversation about it, but by and large that seems to come easily—allowing us our freedom without creating conflict or problems. In fact, we've had zero conflict in the last 18 months.

Until yesterday.

At 10:30 am I received the following text: "How would you feel if I dabbled in prostitution a bit?"

For context, my boyfriend lost his job recently. Mind you he was planning to quit soon anyway to take some time off, so getting fired was actually in line with his plans. Plus he got a very nice golden hand shake, has no debt and healthy savings.

I made a joke about his text because I thought he was joking, but his next response made me realize he was serious. I lost my shit with him. Not just because of the question itself, but because he was texting about something I felt should have been a face-to-face conversation in a private setting at an appropriate time. Also, I was at work and about to walk into a meeting, which did not go well because my mind was all over the place. I mean, seriously, who thinks that's the kind of conversation to have you with your S.O. over text on a Tuesday morning?

I made it clear to him I was upset. He apologized right away. I made clear I didn't want him to make any moves on that until we had a chance to talk. He apologized again and we made plans to talk last night.

I went to his place and laid out that there were two conversations to have. The first being about how he approached the conversation, and the second being my thoughts on his initial inquiry. We got through the first part okay. I explained why the timing and mode of communication had really been shitty, and he owned up to that and apologized. I also thanked him for asking me about it, rather than just running off and doing it in secret, even if he had gone about asking me in a very clumsy way.

So you know, I'm fine with sex work in general. Two of my close friends do occasional sex work. I think it should be legalized and make a point of sticking up for sex workers and porn actors when I hear them being demeaned.

Then we got into the actual question of him considering turning tricks. His immediate response was to say it was a stupid idea and he wouldn't act on it. But I pressed a bit because I wanted to know why he was thinking about doing it in the first place. It didn't seem to me that money was the only driving factor being that he is in good financial shape. He's an attractive guy in his late 20's who has been propositioned by older guys on hook-up apps more than once, and after I pressed a bit more and made sure he knew I had no judgments around sex work in general, he confessed it was in part about having curiosity around the experience of being paid for sex.

In his specific case I found that to be a more compelling reason than his needing to make money. I practice non-monogamy because I don't feel that I own his body or sexuality, and I really want to maintain a relationship that allows us to maximize our experiences in life, rather than pass on opportunities that pique our interest. So if this were a curiosity of his, there's a big part of me that would like him to be able to try it.

After some talking we agreed that he wasn't going to do it right now, and that if he still wants to do it at some later point he can, but we will discuss it in advance, and then discuss it again after he does it, and see how it made us both feel and what our thoughts are at that point. I trust he'll stick to that bargain and feel like it was a pretty good place to leave it.

So after all that backstory, here's my question: Why am I feeling so anxious and uneasy about all of this? We both have sex with other men already, so what's the difference if he's doing that and getting paid for it? (Provided he's keeping himself safe mentally, emotionally and physically.) Despite the fact we're non-monogamous, and despite the fact I'm okay with sex work, the thought of my boyfriend doing it really has my stomach tied in knots, my head in a fog, and my heart beating like crazy.

Am I stupid for entertaining this idea? Or does it make me sex-negative if I don't want him to pursue it? Is that even within my rights to deny him? Am I making a mountain out of a mole hill? I'm really just not sure how to react. I feel like there is serious long-term potential between us, and don't know how giving this a go, or saying no, might affect that.

Please give me some guidance, Dan!

Escort Solicitation Curiosity Opens Relationship Turmoil

You've done so many things right, ESCORT, that I'm not convinced you need my help. Yeah, yeah: you lost your shit when that text arrived. But humans lose their shit from time to time—we are a shit-losing species—what matters is how quickly a person relocates their shit. And you relocated your shit fast, ESCORT, and what came next was everything the advice columnist might order, from calmly listening to your boyfriend express his interest in sex work to being upfront about your own feelings/misgivings. You seem like the very model of modern mature, shit-relocating partner. (Something else that matters in the shit-losing department: the ability to lose your shit without being physically or emotionally violent.)

Moving on to your anxieties...

Quoting your own words, we should all "want to maintain a relationship that allows us to maximize our experiences in life, rather than pass on opportunities that pique our interest." I agree, ESCORT, but I would add that we're also entitled to reasonable boundaries. There will be times in our lives when we have to forgo an opportunity to accommodate a partner's reasonable boundary; there may even be times in our lives when we have to forgo an opportunity to accommodate a partner's irrational insecurity. And while our boundaries—and our insecurities—can shift, evolve, and dissolve over time, ESCORT, some boundaries are forever. Maybe your boyfriend exchanging sex for money is a boundary for you, maybe for now, maybe forever—and that's okay! As Dossie Easton and Janet Hardy say in The Ethical Slut:

Boundaries are how we understand where I end and you begin, where we meet and how we are separate as individuals. You need to figure out what your limits are, what constitutes comfortable distance or closeness between yourself and others in various situations, and particularly the ways in which you and your lovers are different and individual and unique.

Your anxiety could stem from the real risks of sex work. It may help you (and, of course, your boyfriend) to read up on some tips and facts. SWOP USA has a good research page with tips for screening clients, working online, and general health and safety information. But if you're fine with other guys doing sex work, ESCORT, just not your guy... well, then we may be talking about sex work stigma and some unexamined whore-phobia on your part.

As for your specific questions...

"Am I stupid for entertaining this idea?"

Nope.

"Does it make me sex-negative if I don't want him to pursue it?"

Not necessarily.

"Is that even within my rights to deny him?"

You can ask him not to do sex work—you can even make it a condition of being with you—but in the end your boyfriend gets to make up his own mind/make his own choices/set conditions for being with him.

"Am I making a mountain out of a mole hill?"

I think so. It sounds to me like your boyfriend is interested in a sex work as an adventure, not a career choice. (Not that there's anything wrong with the latter.) You're in an open relationship, ESCORT, and he already fucks other guys once in a while. What difference does it make if one or two guys pays for the privilege?