How to Do It

Is It Unhealthy That I Paid My Best Friend to Have Sex With Me?

A man sits on a bed, hand to his neck, as dollar signs flash in the background
Photo illustration by Slate. Photo by dusanpetkovic/iStock/Getty Images Plus.

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

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

Dear How to Do It,

I have a friend I met a few years ago on a dating app. We had sex a couple of times, but it fizzled out. I was kind of confused by this but realized over time that we’re not especially compatible, sexually speaking. But we have remained close platonic friends. She’s the only person I regularly say “I love you” to. She says it too, but we are clear that we are friends and that we will never be sexual together. Occasionally some of our behavior is kind of sexualized (like checking to see if we have compatible kissing styles, or skinny-dipping), but I’ve felt like there were still clear boundaries that we’d never move beyond. I have other friends I have sex with in an ethically nonmonogamous context, so I don’t feel like I’m lacking people I can be physically intimate with.


My friend and I talk about everything, confiding about our dating and sexual (mis)adventures, and offering each other support and care. I feel lucky to have her as my friend. I like to be able to help her out by loaning her small amounts of money, and I gratefully take her emotional support when I go through difficult experiences. Our relationship is genuinely supportive, and not transactional.

My friend does have a history of anxiety and some trauma. I don’t think this in any way defines her, but I think it may be important given the next part of the story.

I recently paid her for sex.

It was her suggestion and had come up once previously before I did it. On the night it occurred, it had come up in conversation as a fantasy of hers. I’d been going through a difficult divorce that had meant I’d had to sell my house and move back in with family. During the conversation, I got a notification on my banking app that a sizable amount of money from the divorce settlement had been paid to me. It felt like the stars were aligned, so I paid some money to her straight away.


The sex was really good. I felt like she really took care to put on a show for me, and I really enjoyed having this experience with somebody I cared about. We checked in with each other a few times afterward. She said she appreciated both the chance to fulfill a fantasy and the money. (She used it to replace a vibrator.) I felt like I had I marked the end of a difficult period having an amazing time with someone I care about. Neither of us regrets it in the least. And I think paying money for it helped. It regulated the exchange, clearly marking this as a temporary change in the rules of our friendship. It also meant that we negotiated how it would work, and where it would begin and end. I can’t help but feel like it was a good thing. But my question—finally—is am I fooling myself, rationalizing an unhealthy lapse in both our judgments?


—Friends With Money

Stoya: I’m not so sure about this sexual (in)compatibility. They seem more compatible than the writer seems to think.

Rich: I wonder what exactly led him to draw the conclusion that they aren’t sexually compatible. He could be hanging it on certain widely accepted hallmarks that in theory suggest compatibility (mutual orgasms, for instance) but don’t necessarily apply to every individual experience.


Stoya: Which would be a shame. I think they should rethink this incompatibility and see if maybe there’s some wiggle room there.

Rich: Well also, in reading the letter, it dawned on me that whatever issues they had previously that led him to that conclusion have been resolved by the payment. They found their mutual interest. Ironed out the kinks, as it were.


Stoya: They’ve found it! Which is beautiful. I do have to mention that the legality of this is dodgy.

Rich: Yes. Not that it should be. I mean, it’s wild that you can pay someone to do virtually anything that one can do legally … except to have sex. You can give someone money. You can have sex with a consenting partner. But combine the two and all of a sudden, the law steps in and says, “Actually … no.” It’s nonsense.

Stoya: Agreed. Two consenting adults should be able to make that choice for themselves. And couples, married and not, give each other money all the time.

Rich: Right, as if rewarding someone for something as nebulous as loving you is somehow morally preferable to cut-and-dried payment for sex.

Stoya: In this particular case, it seems to be a kink, and it doesn’t harm anyone. Nobody is being exploited.

Rich: On the contrary: It allowed them to communicate their desires clearly. I feel that ideally one should be able to do so with any partner, paid or not, prior to sex, but you know, some people need help getting over certain humps.

Stoya: I think our writer is fooling himself to a certain degree. “Checking to see if we have compatible kissing styles” feels pretty sexual to me.

Rich: Yeah, I mean, that almost reads like a fantasy scenario. “Oh I’m doing this … for science.” “I’m Doctor Love and I’m going to examine your mouth with my tongue.”


Stoya: So I’m not the only one somewhat skeptical of the truthfulness of this letter?

Rich: It definitely seems at least a little strange, especially the chain of events regarding his divorce and settlement. I always feel paranoid that someone will troll us by sending in a synopsis of a movie in the hopes of flying under our radar and us taking it seriously.


Stoya: I wouldn’t mind doing that, though. It could make a fun column. Dating advice for rom-coms.

Rich: That particular flourish—”During the conversation, I got a notification on my banking app that a sizable amount of money from the divorce settlement had been paid to me. It felt like the stars were aligned, so I paid some money to her straight away”—feels very scripted. Dating advice for rom-coms is an awesome idea. So many movies are so unrealistic because their plots depend on the bad choices of their characters.


Stoya: This is very true. OK, so this might be an indie rom-com someone saw on a plane. And that would make a great porn script.

Rich: Yes, it’s definitely “edgy.”

Stoya: And yet we’re proceeding as though it is an accurate description of actual events.


Rich: It’s a tough balance to strike, potential bullshit-detecting and giving our writers the dignity of taking them seriously. Dodgy details aside, a scenario involving a flirty pair of former lovers finally finding mutually satisfying ground is, in fact, conceivable.

Stoya: They seem like they’d make great partners for each other. They seem like they already are great partners for each other.

Rich: I hope he paid her more than the cost of a vibrator.


Stoya: Well, yeah. Unless we’re talking one of those gold-plated ones.

Rich: Right. On gay apps, sometimes one finds himself being offered cash for sex. And sometimes the asking price is so low that it’s insulting. Might as well not have bothered! If I’m not advertising my services as paid, you’re gonna have to pay me a lot to turn sex into work!

Stoya: Plus, cheap isn’t generally the most attractive quality.

Rich: Everything you do in the presence of another is communication, including the amount you’re offering to pay someone for sex.

Stoya: Something in the back of my brain is wondering if she wanted a low rate. Like maybe it was part of the fantasy.


Rich: Could be! He doesn’t report any haggling taking place. Do you see anything amiss in this scenario?

Stoya: The only downside I see is the legal status of this particular activity.

Rich: Yeah same. If they’re communicating openly, and if in fact the fee has fostered that openness as described, the “wrong” here is in the realm of the technical (as per the law). “Morally,” and from a sex-positive perspective, they’re good.

More How to Do It

I am a straight woman in her mid-30s married to a wonderful man. I entered this relationship after a very toxic ex nearly destroyed me emotionally and physically, and since then I have always had trust issues. I was recently online on my computer when I noticed that the ads on the sides of the screen were for Ashley Madison. I do not think my husband is cheating, I really don’t, but I still get that jealous pang in my chest when this happens. Is it possible that those ads are showing up because of websites I visit? I do notice that when my husband is on his phone shopping for car parts, I inevitably end up with ads on my Facebook feed for car parts, so I think it’s all interconnected. Am I just in denial?