How to Do It

I Just Discovered the Woman I’m Dating Is a Sex Worker

What should I do?

Photo illustration of a man thinking in bed while a blurred image of a woman leans out of the frame. Neon flame symbols glow in the background.
Photo illustration by Slate. Photo by Wavebreakmedia/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.comNothing’s too small (or big).

Dear How to Do It,

I met a woman on Tinder in April. We hit it off almost immediately from our first date. And soon enough, we started sleeping with each other. There’s a pretty sizable age difference of 20 years, but we made it work. At the beginning, we knew we weren’t exclusive. As time went by, we spent more time together, and it just wasn’t sex anymore. At least not to me. I asked her if she was still sleeping with other people, and she said yes. I tried to break it off, but she said she wouldn’t sleep with anyone else anymore. It sounded like a compromise under pressure, and that’s what it turned out to be: I stupidly went through her messages, and not only hasn’t she stopped, she seems to be sleeping with men for money and is a little flippant about protection. I really like this girl a lot, and but I actually don’t know what to do at this point.

—Side Hustle

Dear Side Hustle,

You say you like this girl a lot, but I’m not sure that you really know her. I think you realize that on some level, and your misguided search through her phone was you acting on that suspicion. Don’t dig through your partners’ phones, social media, or email accounts, please. But you did, and here we are.

If you asked this girl what those messages were about and she said she was sexting as a release and not actually meeting up with people, would you believe her? If not, whatever trust you had may already be irreparably damaged. If you would believe her, you’re gambling with your heart (and possibly your health, if your concerns about protection turn out to be warranted).

You need to think through what you’ll do if she actually is doing sex work to make ends meet or even as her primary career. Sex work is a large field that encompasses everything from offering sexual favors on the street through webcamming and porn. Some people dabble, while others take it very seriously. Ask her. If you’re uncomfortable dating someone in those lines of work, be clear about that with her.

Sit down and have a talk. Come clean about your own boundary violation, apologize, and ask her to shed some light on what you saw. Find out what’s actually going on, and prepare to make some big decisions about whether you’re in or out.

Dear How to Do It,

My boyfriend recently got a VR headset. I’ve seen and experienced VR porn, and it makes me incredibly uncomfortable. I have no problems with my partner watching/masturbating to standard 2D porn. I watch it on my own, sometimes watch it with my partner to set the mood, have it on during sex, etc. However, I feel VR porn crosses a line. It changes the role of the individual from being a “watcher” to being “directly involved,” and that role shift isn’t OK with me. At the push of a button, my boyfriend can take part in “perfect” sexual situations with the “perfect” partner. I explained these reasons to my boyfriend. He said made it very clear he doesn’t understand my perspective, doesn’t intend to stop, and will try more VR porn with different levels of involvement.

I try to be laid back in my relationships and don’t have a list of deal-breakers. I’m really struggling to get past this, though. I understand and respect that I can’t keep him from VR porn. That said, I’m confused as to how I should navigate the situation. Is there another perspective I might be missing, or maybe a good side to this? Am I uncomfortable for nothing?

—Colored Glasses

Dear Colored Glasses,

I’m curious whether two-dimensional POV porn also bothers you. After all, it’s the lower-tech version of these VR scenes that are being churned out. If it doesn’t bother you, maybe that’s your entry point to VR—it’s just a 3D version of some other non-bothersome porn. I’d also note that many people imagine themselves “directly involved” even with 2D porn scenes. Have you never fantasized that you’re the person in the porn you watch?

I wonder whether there’s something going on with your self-esteem or confidence in what you bring to the table, physically. When you talk about “perfect” sexual situations with “perfect” partners, there’s an unspoken comparison to your less-than-perfect body or life. Do you feel lackluster or insecure? If so, nobody and no amount of porn bans can fix that for you. Therapy might be helpful. A workout routine might be useful, too—not so much for losing weight as for energy, confidence, and mental health.

As for the additional perspective and “good side” to VR porn you seek, I think you should ask your boyfriend about this. He is the absolute best person to fill you in on what he finds appealing about VR porn and what he enjoys about it. An open, neutral conversation about the subject might help you understand more and feel better in general. (I can’t tell you much from personal experience about VR porn because VR headsets give me a headache—which I’m told may have something to do with gender bias during the engineering phase, at least as of a few years ago.)

All this said, your discomfort is valid. Feelings don’t mean you (or your boyfriend) have to do anything or make any changes, but they still happen and need to be honored and felt. Take a page from Emily Nagoski and think of those feelings as a hedgehog sleeping in your lap. Be gentle with them. They’re yours—they’re in your lap, not your partner’s. It might be helpful to write out exactly what threatens you about VR porn, and meditate on the why’s of each point: Get to the root of what’s bothering you, so you can make useful, adaptive requests and suggestions for compromises where both you and your boyfriend feel comfortable.

Dear How to Do It,

I am feeling so lost. I have been with my partner for nearly 15 years. We have had three children together, the youngest of which is almost 6; the oldest just turned 9. Our sexual relationship is currently ho-hum at best, and began in my late 20s and his early 30s. It was amazing at first, but fell away. (I had been with a woman for six years prior so the idea of “turning” me was hot, I suspect, and he had a vast number of partners in his youth—55+). Now we rarely have sex once per week, and it is satisfying but obligatory at best. No heat, no want, no passion. I desperately want more. I find him attractive and am open to a wide variety of interests/kink. He is not. I have shared a few interests of mine, but they have been quickly and summarily rejected.

He tells me there could be desire and passion in our relationship if we were both “hot and attractive and lost weight.” We are both rapidly nearing 50. I am average to slightly overweight, and he is (being generous) the same. He does not “manscape” and when he does, asks me to assist if our summer social outings involve others (not in a hot co-showering way, but in a we-are-going-to-a-pool way).

I want him. I want to be with him and desperately want him to want me. I can think of numerous scenarios that turn me on, and there are very few proclivities I could ever see myself rejecting. I will never be the hot, tight, pre-children woman he dreams of. I am completely average (5’8”, 145 pounds) and madly in love with him. I love sex. I love sex with him. But sex with us is currently completely compulsory, oftentimes rare, always fine/mostly satisfying, but not hot or passionate in any way. I want more. I need more. I feel like we both deserve more. Other than getting head-to-toe-surgery or starving or living in the gym, what do I do? This is not new to us, but recently I have found myself feeling so extra lost, lonely, and rejected. Not ready to destroy my family over this, but also not willing to give up my sexuality and desire for the rest of my days. (An open relationship is not an option.) Help?

—Lost

Dear Lost,

You’re married to a man who meets your requests to engage in sexual activity with derision and body shaming, you’re not willing to leave him, and an open relationship is not an option. I can suggest masturbation and props: books, toys, graphic novels, and vibrators. But that won’t give you sexual interaction with your partner. You can’t get in a time machine, you can’t make him want you, and you—for your own reasons—can’t leave. Based on what you’ve written to me, I can’t help you, not until you’re willing to take your own needs more seriously. I wish you luck.

Dear How to Do It,

I am a gay trans man on the autism spectrum with both generalized and social anxiety, and I have a phobia-level fear of STI transmission and pregnancy. What all of this amounts to is a fussiness around sexual safety that goes way beyond what most people consider reasonable (e.g., barrier methods even for hand and mouth stuff, and I don’t like open-mouth kissing). I dislike all body fluids—spit, urine, blood—but semen is the most anxiety-inducing for me because of my absolute terror of pregnancy (even though I refuse to be the receptive partner during penetrative sex, so it’s not really a risk).

To be clear, I know, logically, that most STIs are treatable, the incurable ones are manageable, and that abortion is still an option—but my experience of generalized anxiety means that there is no subjective difference in my experience of risk, and that any risk feels the same as basically a guarantee. I also grew up in a family which had a very conservative Christian attitude toward sex, and thus probably a lot of my hangups are attached to feelings of shame and punishment over “bad” things happening because of sex.

Most of the time, I’m OK with being indefinitely single and celibate. I don’t have a high sex drive, and I have plenty of stuff that keeps my life full and busy. But sometimes I get really sad about it—I still yearn for a kind of physical intimacy that is usually restricted to sexual/romantic relationships, and I avoid gay media and even the gay community because I’m only at peace with my apparently permanent singleness when I don’t think about it too much. I live in a fairly large city, but not one which is famous for its LGBTQ population or culture. Is there any point to trying to meet people for dating or sex with my hangups? I’m not a very attractive person by most standards, and I worry the only people who would be willing to lower themselves to my level would be fetishistic creeps who would only want to have sex with me in a way I’m not even interested in.

—Fear and Loathing

Dear Fear and Loathing, 

That last line sounds alarmingly like incel talk to me. I hope you’re in therapy and that you’ve shared this sentiment with your therapist.

Somewhere out there is a person who is just as afraid of germs and semen as you are, or isn’t particularly interested in sex (maybe a gray or asexual) but is into cuddling and the kind of intimacy you crave. Get in there with your therapist and do the work so you’re ready to accept his affection when he appears, rather than telling him you’re a hideous troll and don’t understand why he could possibly want to spend time with you. That “hideous troll” bit can be a real turn-off. Therapy can also help you confront your social fears and work through your internalized religious shame.

In the meantime, focus on the stuff that “keeps your life full and busy.” Get your career in order. If you need further education, make moves toward that. Find your direction in life. Develop a hobby. Put energy into things that make people interesting and attractive to others. Maybe consider moving to a more LGBTQ-centric city. Anything that equals more potential matches for your very specific needs.

Consider going to LGBTQ community events and sitting with your jealousy. Let it inform you about what you want. Feel your jealousy, and listen for clues about your ideal life. Try smiling when you see a couple you wish you were a part of. Meet people for the sake of meeting them. Be content with friends when you find them. You sound like you’ve already overcome a lot to be the person you are, and this hurdle shouldn’t be insurmountable.

—Stoya

More Advice From Slate

I consider myself a decent man, but for the past year I have been cheating on my wife about twice a month with prostitutes. We’ve been married for more than a decade and have three young children. Since the beginning of our relationship, my libido has exceeded hers, and she frequently refused my overtures. Now we have sex about once a month, only when initiated by her, because I became so resentful about being rebuffed constantly. It’s mutually satisfying but bland. We get along reasonably well, and our children are our chief priority, but we are emotionally disconnected. Out of despair and frustration, I saw an escort last year. The thrill of seeing prostitutes and the variation from my usual sex life made me feel better, and I think it’s more honorable than an affair, but it is the worst thing I’ve ever done. If my wife found out it would lead to the immediate dissolution of our marriage. We have talked about counseling, but she’s not very interested. If we divorced it would devastate my children and would deprive me of seeing them every day. My plan right now is to continue what I’m doing until the children are in high school and college, then get a divorce. Is there another way out of my dilemma?