How to Do It

I Want to Marry the Woman I Pay to Have Sex With Me

I know this isn’t realistic, but …

An older man and younger woman flirting with a neon dollar sign flying in neon.
Photo illustration by Slate. Photo by Olga Balynska/iStock/Getty Images Plus.

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,

I’m in a bit of a quandary. I’m a middle-aged professional man who’s been divorced over a year and a half now after a 20-year marriage. I live in a small town, my extended family lives far away, and there’s not much opportunity to make friends. My support network is very limited. I’ve tried online dating and that’s gotten me nowhere. So, because of loneliness and boredom, I sought out the services of a sex worker. I have now seen her many times, and she is amazing! When I’m with her, we seem to connect not just sexually, but emotionally as well. I do realize it is her job to make me feel good, but I have now developed feelings for her. I’m starting to get jealous, thinking of other people she sleeps with. I think about her day and night. I’ve spent tens of thousands of dollars on her, on gifts, vacations, etc. I’m trying to stanch these feelings, because I know that in the end this relationship is going nowhere. I’m trying to accept her for who she is, but these negative jealous feelings get in the way. I’m reluctant to stop seeing her, since she checks all my boxes and fulfills me on multiple levels. Can you give me suggestions on how to think of her as a Friend With Lovely Benefits, and not as a Fiancée in Waiting?

—Pretty Woman

Dear Pretty Woman,

Reread your own words: “I do realize it is her job to make me feel good”; “I know that in the end this relationship is going nowhere.” You know all you need to know. I encourage you to focus on your analysis, instead of your emotions. It’s sweet, I guess, that you caught feelings, and sex and one-on-one time can certainly facilitate them, but that sex came as the result of a contract you entered into with this other person. It sounds to me like she’s just really good at her job, and you can’t expect more than that. Just as you wouldn’t ask your accountant to bake you a pie because he’s so good with proportions, or a court stenographer to knit you a scarf because of her nimble fingers, you shouldn’t go asking a sex worker for love. She’s not even your friend with benefits—you two are in business together. I’m sure it feels uncontrollable, but your jealousy bespeaks a certain entitlement that I’m not into at all.

However, I suppose there is a not-zero percent chance that she has developed feelings for you as well. Put two people in a room together, they might fall in love. You never know. If you want to test it, you could tell her how you feel and ask to see her for free. If she’s into it, OK. If not, that answer will hopefully provide the rude awakening you need. Accept it.

Dear How to Do It,

Recently, I noticed a social media notification on my phone that suddenly disappeared. I don’t post a lot, so it was unusual. Curious, I checked the username (the notification was also emailed), and I found that it belonged to a man I dated briefly. We haven’t talked for nearly a year and a half. He must have “liked” one of my posts when he was lurking on my account, then quickly undid it. Well, I scrolled through his posts, and was surprised and dismayed to see “subtweets” about me in his feed! The first one I saw said something to the effect of, “The last man I dated said he just wanted to be friends because he had to focus on his immigration status. I just saw him on a dating site. Men will do anything to avoid commitment.” (I was working on a visa at the time, but he was also clingy, so I tried to cut it off kindly.) There were other tweets that referred to me. It makes me uneasy that he would post these things, and now I have reason to believe he was creeping on my social media accounts when we hadn’t talked in more than a year. Am I overreacting, or is this a strange fixation? I almost want to delete my online presence.


Dear Subtweeted,

You hurt a sensitive person’s feelings, and it’s taking him time to get over it. I don’t condone his subtweeting or apparent distortion of facts for the sake of social media performance, but think of it this way: It would be far more annoying if he were contacting you directly about this stuff instead of pissing his thoughts into Twitter’s cesspool. Social media took him off your hands.

You may think you have the moral high ground here, and I even kind of agree with you if I’m nitpicking (he started it!), but speaking in purely practical terms: His lurking on you disturbed you, so you … lurked on him back. Game seems even at this point. As you well know, when you keep a public feed, you are implicitly allowing anyone and everyone to check in. You knew he was clingy; I just can’t believe that you’re totally surprised by this development.

Limit public access to your accounts (by making your Twitter private, for example). Do not engage with him. He seems dramatic. And when in doubt, live by these golden words: Never tweet. Believe me, it’s a hard lesson to learn, but it’s worth striving for.

Dear How to Do It,

I’m a 20-year-old woman who’s been dating a 23-year-old for a little more than a year and a half. He is absolutely wonderful and has helped me through various extremely rough periods since we began dating. But there is one thing I have not been able to get past, which is now affecting our sex life: Two years ago, to the day that I am writing this, I was raped by my now-ex, just days after my 18th birthday. I told him I did not want to do anything physical and laid down for a nap, and as I slept, he raped me. It took me three months to come to terms with this and end the relationship, during which time he got more and more aggressive and dismissive of my needs or desires, just doing whatever he wanted, whenever he wanted, no matter if I was in pain or begging him to stop.

I was so ashamed of all of this that I didn’t tell my current partner for nearly a year. He has been very supportive and wonderful since then and has always helped me however I needed. But lately, every time we start to get physical, I flash back to my ex and what he did to me. And I just shut down. I have tried seeing a therapist, but it has not been very helpful. Now, in my state, my time to report my ex has come to an end. I feel like I will never get closure from my abuse. I worry that I will never be able to have a fulfilling sex life ever again. When my partner and I began dating, we would have sex two or three times a day most days, but now it’s closer to once or twice a month.

I still have sexual desires, he’s still incredibly attractive, and his sex drive is still just as high as it was when we began dating. But I just can’t bring myself to forget what I’ve been through. I have no problem masturbating, but once he touches me, I freak out. And while he has never pressured me once I say no, I know he is disappointed that we don’t have sex as often, and I find myself feeling extreme guilt and occasionally forcing myself to do things when I would rather not. I want to get back to how things used to be, but I can’t get past my abuse. What should I do?

—Ex Memories

Dear Ex Memories,

I’m really sorry your ex did this to you. You’re not alone—we get letters like this a lot—and they always sadden me. Abuse ruins lives. The act (or acts) itself is one thing, and then you’re left to deal with its effects for who knows how long. It just isn’t fair.

You say a therapist wasn’t helpful, but I think you could really benefit from someone who specializes in this kind of trauma. I don’t know what your financial situation is, or how long it may take you to find a better professional, but in the meantime (which is to say right now), consider calling RAINN’s National Sexual Assault Telephone Hotline at 800-656-HOPE. The person on the line will be able to talk to you about what happened, as well as refer you to support in your area.

Beyond that, there’s quite a bit that you can do to heal—last year, I spoke with (retired) sex therapist and author Wendy Maltz, who’s written extensively on this subject and walked me through the reconditioning process she prescribes (see the the last question). You could check out that link, but I wouldn’t do anything before speaking with a more qualified professional. It sounds like your boyfriend is a good fit, given your situation (provided that he’s never pressuring you ever, and not voicing the disappointment you are detecting). I know it may be difficult, but try not to get bogged down with guilt: You didn’t choose what your ex did to you. And I really don’t recommend forcing yourself to do anything you aren’t comfortable with. The risk of retraumatizing yourself is not worth it.

This isn’t likely to be a quick or easy process, but with patience and care, you can heal. You are not broken. Best of luck.

Dear How to Do It,

I’ve been married for 20-plus years. The last 10 years have been mostly platonic, which I hate. My husband doesn’t want a physical relationship with me at any level unless I threaten to leave him. Which I did, and things improved briefly because he was desperate to keep me from leaving, but I don’t want to force him to do something he seems to dislike. We have a great life together, except that he appears to hate touching my bare skin. I wish I could have a fling, and I think he would be OK with it as long as I don’t leave him. But how would that even be possible? I’m a 58-year-old woman! I look good for my age, but my age ain’t young. And I don’t know how I would possibly find a man who is able and willing. And I don’t want to be a homewrecker, either. Should I just be content with a vibrator and my good, but celibate, life, and reminisce about the sexy days gone by? Is there some secret club for middle-aged people whose spouses don’t like having physical contact?


Dear W4M,

Oh, it’s possible: This column alone gets dozens of letters a month from men around your age who are similarly seeking casual sex but feel similarly helpless about finding a partner for it. Perhaps How to Do It should develop (or full-on pivot to) a middle-aged hook-up app. In the meantime, don’t just assume that your husband would be OK with a fling—talk to him about it. With the evidence you provided, it sounds to me like he will, in fact, be amenable so long as you don’t leave. Be sure of it, and you’ll find yourself in a common open-relationship scenario. I know that you may not consider yourself a senior citizen (and some dictionaries might agree), but I recently reached out to a senior-sex advocate, writer, and educator Joan Price, who told me that OkCupid and have a lot of older users. I’m sure many are looking for relationships, but presumably many would be down for something more casual. Hell, an age-filtered Tinder might even work. Where there are apps, there are horny people of all stripes.


More How to Do It

What is up with this: My husband (we’re straight) and a few of his circle of friends seem to have this flirtatious homoerotic thing going on where they pretend to—or actually do, in the guise of a joke— flirt, rub each other’s shoulders or thighs, and make breathy jokes about each other. My husband would hate it if it were me and my friends acting like we were about to make out. And I have said as much. But he doesn’t say anything to his friends in the moment, and their wives and I often joke about it, like “so and so is going to run off with your husband, hahahah.” I want to know if I’m in the right to be ticked off.