How to Do It

I’m Afraid My Boyfriend Will Lose It When He Finds Out About My Secret Past

A man and a woman kissing, as money flashes in the background.
Photo illustration by Slate. Photo by 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 a 24-year-old woman with a 27-year-old guy. We’ve been together for almost a year, and he’s one of the most amazing, inspiring people I’ve ever met. I see myself becoming family with him. But I’m struggling with how to tell him about my past.

A couple of years ago, I had not yet been treated for certain mental health things, and I was not stable. I was looking for life because it didn’t feel like I had much life left in me. I turned to selling my body to older men. I didn’t need the money— I was mostly looking to be wanted and appreciated, and used. Then I got treatment, and I started a life that’s almost a dream. The thing is, I don’t regret my past: It created this version of me. I am strong now. I know what’s right for me. I live for my values, and I am healthy. My boyfriend has been very kind and patient with my mental health (though I have shame around those details too) and with some sexual trauma issues, but I’m afraid this will really alter how he sees me. What if this dampens and extinguishes the excitement and trust that is so precious to us? What if he sees me differently after this conversation? I want our closeness to grow stronger, and not wither from such details. Some of which are horrible. What should I do?

—A Few Ghosts

Dear A Few Ghosts,

I think you should wait a bit longer and collect some more information before revealing this part of your past. While it can feel natural to share a detailed biography with your partner, it is not strictly necessary to tell him everything that happened in your life, nor is it technically possible. Your sex work made you who you are today, but if it did only that and left you without obligations (of the legal or professional sorts) that affect your current life, it’s hardly need-to-know information—unlike, say, your ongoing work on your mental health and sexual trauma issues, which it sounds like you’re communicating well. If there is literally no reason beyond the abstract notion of closeness to tell your boyfriend about your former job, find other ways to foster closeness for now.

Wait until the subject of sex work comes up, evaluate his potential reaction from that, and then proceed accordingly. If he has huge moral qualms with it, it’s your chance to teach him that it’s honest work, despite what the law might say. Or, if his response is particularly virulent, you can make up your mind from that whether he’s the kind of partner you actually want to be with. Or you can decide to keep it as your secret. You’re allowed to have things you keep to yourself. That doesn’t necessarily make you deceptive, it might just make you practical.

Dear How to Do It,

I’m a man almost in his 30s, and I have mommy issues—or, to be more precise, strict-older-women issues. I was raised by a single mother who punished me by making me pull down my pants for spankings, I was sexually abused by an aunt, sexually assaulted by a teacher (hands on my crotch), sexually harassed by a boss (nudes at work), and I sometimes can’t get hard without fantasizing about them or about mother-son incest porn. I know I have issues and experiences that I should see someone about, but the women in my life were all great mother figures when you exclude everything sexual. All I want to do right now is to date and have sex with no-nonsense women who let me call them “Mom” as I’m inside them. It’s gotten to the point where it’s all I desire. I have a great fantasy life, and I haven’t had sex in more than a year because of it. I’d like to enjoy sex again—but I can’t honestly say that I enjoyed sex all that much compared to my fantasies. Help? I’m terrified of revealing this side of myself, since the consequences for and the chances of being misunderstood are immense.

—Bad Son

Dear Bad Son,

You seem confident that you can extricate the abuse you endured from the overall experience of being mothered by various figures, but it seems pretty clear to me that you can’t. That’s a reason for therapy, not against it, as your “but…” construction suggests. Your fetish is what it is, and it’s not as though no one else shares it and the world is free of prospective mommies for you, but I can’t responsibly tell you to pursue your interests without imploring you to sort out their apparent traumatic roots with the help of a professional. Kink apps and self-identifying MILFs, who may or may not be OK with being called “Mom” during sex, will still be around after you probe deeper from within. It’s not like you’re pursuing your interests at the moment anyway, so you might as well talk to someone who can help make sure that you’re pointed in the right direction when you finally do.

Dear How to Do It,

My partner and I (both men) are very much in love. We talk about kids; he recently met my family; and we just moved in together after moving across the country. The problem: While I don’t doubt his affinity or commitment, he’s clearly uncomfortable with the fact that I’m HIV positive. We’ve locked down together, but it was only during our move that I noticed his aversion to sharing toothpaste, commingling our dirty laundry, and showering together. He’s fine with sex, but (understandably) only when on PrEP—and he’s consistently missed a dose here or there. He’s so frequently missed a dose, and declares that just as things get heated, that I’m beginning to believe it’s an excuse. I want to make this relationship work, but it took me a long time not to feel radioactive after getting my poz diagnosis. Given all the science around transmissibility while undetectable—which I am—am I wrong to be offended by the toothpaste, laundry, and PrEP inconsistency?


Dear Poz,

You are not wrong to be offended. I’m offended after reading your letter. In 2020, this level of ignorance about HIV is willful, and I would expect someone who’s very much in love with you to be doing what he can to educate himself. It’s a red flag that he isn’t. I’m not even talking about reading a book; he could read a Wikipedia entry. He could scan pithy summaries of the landmark PARTNER studies, which were crucial in demonstrating that undetectable means untransmittable and documented zero HIV transmissions in sero-different couples (the second PARTNER study surveyed nearly 800 gay couples after 77,000 condomless sex acts). Your guy is stuck on toothpaste and laundry, which puts him squarely in a plague-years mindset. For your purposes, he might as well be living in the dark ages. You can either attempt to educate him, which given all the effort you’ve put into living together seems like the most prudent route, or kick him to the curb and find someone with a clue.

Dear How to Do It,

I am in my late 60s, and my wife is in her mid 70s. When we met some 40 years ago when I was just ending my first marriage to my high school sweetheart, the only woman I had ever had sex with. My current wife, six years my senior, had many lovers and all the wild sex I craved. We both have very high sex drives and still do. After 2 ½ years of copious but vanilla sex, I was concerned that if this relationship continued, I would never get to experience what she had, so we separated. A few months later, with my sexual adventures off to a slow start, we met up. We both still loved each other, and I wanted to have sex with her so badly. She said no way—marry me if you want sex. Since I still loved her, at 29, I agreed to marry the second woman I ever had sex with. Since she had such a colorful and exciting sex life before me, I just figured this would carry over into our relationship. She would feed me tidbits of her exploits when prodded. In our younger years, I often suggested we try swinging, threesomes, clubs, anything. It was always just about sex, but still, no way. She was done with that. I love her dearly and accepted my fate. Our vanilla sex has continued to this day. We have tried role playing, toys, etc., which helped a little, but not much. I would never cheat on her. I feel like a sexual failure, and rarely feel satisfied. She is content with our sex life. To make matters worse, she has now admitted if I was more aggressive back then, she would have agreed. I feel like such a fool. She says move on, get over it, but I cannot. Is there something wrong with me?

—Missed Opportunity

Dear MO,

From what you have presented, there isn’t anything wrong with you, per se, but your thinking patterns are setting you up to feel that way. Comparing yourself to others, which you cast as the impetus for your own sexual exploration in your 20s, is a path to misery. If you attain your goal, it may only bring you to an arbitrarily defined equilibrium, and if you fall short, you are acutely aware of what you think you’re missing. Your 40 years of chronic FOMO is a case in point.

What about your life, which includes a high sex drive in your late 60s, makes you feel like a sexual failure? For a moment, ignore what you don’t have and focus on what you do. Many people would envy a marriage like yours. Your satisfaction is another matter—if your wife is unwilling to accommodate your needs and nonmonogamy is out of the question, well, you’re effectively settling. You have enough time notched to understand the tradeoff: You are forgoing the excitement of casual, even fully gratifying sex, for the continued presence of your wife. You have made this choice because you figured it to be worth it; if you are reconsidering, perhaps you are realizing that it isn’t.

It was really shitty of your wife to say that you should have pursued your nonmonogamous interests more aggressively, as it’s reasonable to assume that you did not out of respect. But there’s nothing you can do about that now unless this is her way of critiquing your overall approach and requesting a more aggressive sexual atmosphere. Don’t presume that it is, but do talk to her about the message behind her if-only scenario. A counselor might help you here—if you feel as unhappy as you do, even if it’s irrational, you may have to work with a professional to find your happiness and you may need your wife by your side to do it.

More How to Do It

I got involved with an older married man a few months ago knowing that he had no intention of changing his situation. He told me he was looking for a female friend to fill the void in his sexual life because when his wife went through menopause eight years ago, she lost all interest in sex. We eventually developed deep feelings for each other. He admitted it in a series of texts and conversations. I broke off things with him at least three times since, knowing this situation was morally wrong. We have since resumed our relationship again. My question: Aside from him lying to his wife about his whereabouts when we are together, do you think he is lying to me too about his feelings or the situation with his wife?