I Want to Be Open About a Certain Part of My Past. But Men Always Take It the Wrong Way.

Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!)

Dear How to Do It,

I (46F) met a (44M) who seemed charming. But, on the second date, he started to tell me about his vices. He failed school due to coke addiction and he is a casual smoker. I thought, well he has his life together now and I can tolerate a rare cigarette. Then, after his third drink, he confessed that he still does coke and just left alcohol rehab! His personality changed and he got sullen about his inability to keep relationships. He then begged me to sleep with him .I was uncomfortable and didn’t trust him but I tried to empathize. I told him I also had things I wasn’t proud of and had enjoyed casual sex but now wanted monogamy and to get to know someone first.

He freaked out, demanded to know how many people I had slept with, and then ended the date and escorted me out of the bar. He texted me saying how sad he was that he couldn’t date a woman like me because of my history. I was royally pissed that he slut shamed me after I listened to him with compassion. I told him not to feel sad, he did me a favor, and that at least my “addiction” brought couples together instead of tearing them apart. He said that I used his past against him which proved what a horrible person I am and that he made the right choice about me.

This guy is a hypocritical jerk and I never should have told him anything. But the incident has me doubting what I share with new men and when. I want my partner to know who I am. I’ve slept around a lot but I’m super loyal in a relationship. Is there a right way to own my inner slut without being judged for it?

—Wants to Be Slut Praised

Dear Wants to Be Slut Praised,

There probably is a right way for you to own your “inner slut,” but there’s no guarantee that any specific procedure will prevent you from experiencing judgment. Dating with the goal of finding a partner does involve judgment, on the part of everyone involved, in the sense that you’re considering whether the person you’re dating is someone you can build a healthy relationship with. Remember that each man is different. Some will absolutely react by shaming you, and they’re letting you know that they aren’t for you. Some will celebrate your sexual history. And others won’t have strong feelings either way. This particular guy was aggressive, rude, and excessive, though. I suggest blocking his number.

It’s worth thinking about what sort of acceptance you want from your future partner. Imagine possibilities from a shrug to a regular request to hear stories as part of your flirtation or sexual interactions. It’s also worth defining what monogamy means to you—both for your own behavior and that of your partner. Do you want to have a relationship where you speak openly about current attractions and past antics, while remaining physically monogamous? Do you want to share these stories once and never speak of them again?

My situation is different from yours—I’m less inclined toward anonymous hook-ups in recent years, but I’m involved with multiple people simultaneously. And keeping my sexual adventures secret isn’t very likely, considering that many were recorded in HD video and heavily marketed online. But I think the broad strokes of how I do it may be useful. On the app itself or during a coffee that can be easily fled, I’ll let the person know that I’m a sex columnist, which often prompts a question of how I got into this line of work. When I broach the subject of my career in pornography, I pay attention to how they respond. I’m also braced for a sudden shift in tone, like what you experienced, and am aware that this shift often comes weeks or months later, when they’re confronted with the reality of my work. I put effort into active transparency so we can both have an idea of how they’ll react before anyone gets too attached. You’ll have to evaluate your own goals and needs within your relationships, what you’re willing to be vulnerable about, and how much of other people’s projected shame you’re open to experiencing to figure out your own way.

From: The Men I Date Might Always Use My Past Against Me. (February 21st, 2023).

Get advice—submit a question!

Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.

Thanks! Your question has been submitted.

Dear How to Do It,

My husband and I are in our late 40s, having been married for 16 years and together longer than that. We both recently and completely separately got promotions at our respective jobs, which means a sudden huge boost to the household income and a serious urge to celebrate. We managed to get the kids to spend a weekend with their cousins and decided to party it up while they were gone. Part of that partying involved hiring an escort. I don’t want to reveal where we live, but this is perfectly legal where we are, as long as you do it through an agency. A very nice young woman, let’s call her “Daisy,” came over shortly before noon and stayed until maybe 8:30. There was a lot of sex, and everyone enjoyed themselves. But there is one part of it that gave me a little pause.

It was getting near suppertime, and while my husband and I had broken off to eat a bit, Daisy hadn’t had anything except some water she had brought with her. We were planning on ordering some food and asked if she wanted anything, especially since she hadn’t eaten since at least lunchtime. She got this almost frightened look and said she wasn’t supposed to take food from clients. But then, about a second later, she said she would like some vegetable rolls but we absolutely had to promise not to tell anyone. We do this, order the food, and she practically tears those rolls apart. Again, she asks us not to tell anyone before she eventually leaves later on.

I want to be sex-positive and support sex workers. And I hope we didn’t make some kind of faux pas or caused some kind of trouble for Daisy. But it was strange and didn’t make any sense that she couldn’t eat on the job, especially if we were feeding her. And, I mean, we had her over for almost nine hours—of course she’d get hungry in the meantime. What exactly is she supposed to do? Did we do something awful that we should try to make amends for?

—Not Used to This

Dear Not Used to This,

You didn’t do anything awful you need to make amends for. And if Daisy broke some rule of her agency or booker, the last thing you should do is draw attention to it by making an apology.When I first started appearing at conventions, I was warned against taking food or drink from attendees. Even accepting a sealed bottle of soda or water would get a skeptical eye from some more experienced co-workers. The reason being that while most people are, well, not trying to drug you (for nefarious reasons, no less), someone might be. Daisy might have weighed her hunger and made a judgment call based on the fact that the food was coming from a restaurant. Nine hours is a long time to go without food, though, so I’m puzzled as to why she didn’t bring her own. If you decide to hire an escort again for a long session, you might mention your absolutely normal habit of eating regularly to the agency and see what they say. You might try something like “We’ll be ordering dinner halfway through and want to know whether Roxie has any dietary restrictions.”

From: My Husband and I Hired a Sex Worker. Then I Think We Crossed a Line. (November 28th, 2023).

Dear How to Do It,

I am living in the most frustrating dream scenario possible. About three months ago, I started dating my long-term best friend. We’re a perfect match and stupidly attracted to each other, but our sex life has been floundering recently. Ironically, being friends for so long is the problem.Every time I try to initiate something, he takes it in a friendly way. The other day, I asked as seductively as I could if he felt like doing anything that night. He said (in a very monotone voice), “Sure. Uno sound good?” Maybe we’re doomed to forever have a bromance instead of a romance, but I don’t want to give up too quick! I know it’s a problem he’s having, too. One time, we were playing a video game when he mentioned wanting to ravage me. I blanked and responded with “player vs. player is off,” and haven’t lived it down yet.

So, advice? We’ve had sex, but it’s usually on formal dates, which are pre-established to be more than “just friendly.” Asking for it outside that rarely pans out.

— Best Friends Forever

Dear Best Friends Forever,

If asking for sex outside of preplanned dates doesn’t pan out, why don’t you just go on more dates? If there’s something more erotically stimulating about the formality of dates (perhaps they contrast explicitly with your usual hangs enough to make what used to be friend shit feel differently), well, lean into that. But I’ll tell you: It sounds like he’s having second thoughts. People feel out sexual chemistry in real time and a strong friend connection or even a strong aesthetic attraction does not guarantee satisfaction. Could it be that you aren’t a good sexual fit? Could it be that he’s trying to tell you that he just doesn’t want to continue exploring that arena with you? Yes and yes. The unfortunate thing about these situations is that not everyone involved is necessarily aware of the disconnect afoot, especially when there is a party, ahem, who is super enthusiastic about making things work.

Different people move at different speeds, so take this generalizing with a grain of salt: Three months in is really early to be experiencing bed death. If you are such good friends, you should be able to talk about this. That seems so obvious that I suspect you’re writing in instead of having that conversation because you fear its outcome. However, it is better for you to know now, before you get more romantically invested in something that’s just not going to work out. Your assessment could be spot on—sometimes the better we know people, the less erotically appetizing they are (which is why Esther Perel prescribes distancing and mystifying techniques to keep the sexual fires burning). If this is the case, you could mourn it as an ironic tragedy—too close to be sexually compatible!—or you could be thankful that you tried it out and received back information that you’re just better as friends. A good friend is a good thing, so ending this chapter of your relationship wouldn’t be the end of the world.

From: My Bromance Is Finally Becoming a Romance. We Just Can’t Seem to Stop Acting Like Bros. (July 24th, 2022).

More Sex Advice From Slate

I keep having negative reactions to lube! They either trigger yeast infections or cause immediate burning as soon as they touch my skin. I’ve run through most of the ones commonly found in big-box stores and a bunch of the popular specialty ones available online. How do I find a lube that won’t do this? Trial and error is getting pricey, and it’s painful.