Dear Prudence

I Can’t Stop Cheating On My Wife

I don’t want to blow up my perfect life—or stop seeing other women.

A row of women make kissy faces at a bearded man.
Photo illustration by Slate. Photo by wernerimages/iStock/Getty Images Plus, master1305/iStock/Getty Images Plus, and Deagreez/iStock/Getty Images Plus.

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Dear Prudence,

I’m a man in my mid-30s with a beautiful wife. We’ve been married for 15 years and had a great kid very early on in our relationship. We both have great careers, nice friends, a very kinky and active sex life. Others generally look at us with admiration and envy. My problem is that I became a serial cheater around eight years ago. I analyzed quite a lot why I feel the need to cheat (sex with my wife is definitely better than with other women) and think that I like the challenge of “conquering” and later the romantic aspects of it. My affairs usually last a few months. I’m also very open with my relationship status (and my unwillingness to change it) to my affair partners. I even developed great friendships with two last affair partners, and the whole experience has generally been extremely enriching and positive for me.

I never fell in love with another woman, and I want to stay with my wife forever, but I can’t seem, and also don’t want, to stop seeing other women. My job involves a lot of travel, so it’s easy to get away with cheating without arousing suspicion. In the beginning I didn’t really think too hard about it, but going forward I want to be “square and fair.” My wife doesn’t have the slightest idea of my cheating and would obviously be devastated if she found out.

A year or so ago I started talking about opening up our relationship as a way to slowly “legalize” my behavior. While she isn’t totally against the idea, it’s more something she can imagine in a distant future and in a very controlled setting. I reckon that the romantic aspects and durations of my affairs would be serious no-gos for her. While the easy answer would be “stop before you blow up your perfect life,” I feel like I’m not really able to. What are your thoughts?

—Can’t Stop Won’t Stop

Many people who cheat on their partners enjoy it—that’s kind of the point, and there’s nothing unique about the fact that you like something you do expressly for your own selfish ends. Cheating is designed to be enjoyable, as long as you don’t spend too much time thinking about how your partner might feel about it. And for whatever it’s worth, I don’t think you have a “perfect life,” and I imagine not everyone looks at you with admiration and envy. I think you have a very precarious and compartmentalized life, one that could likely fall apart in more ways than one.

You have a few options, as I see them: continue cheating on your wife and hope she never figures it out (or if she does figure it out, she suffers alone and in silence and never bothers you with her anguish). There’s a decent chance you’ll be able to pull that one off, although you’ll never feel secure about it until the day one of you dies. (Plus, there’s always the possibility that it’ll come out somehow after you die.) You can also stop cheating on your wife, which you are perfectly capable of doing. You are a human being with the ability to choose his own actions, not an infidelity robot that’s been accidentally set to chaos mode. Most crucially, I think you need to abandon the delusion that you’re going to be able to acclimate your wife to the idea of an open relationship, since the terms upon which it would interest her seem vastly different from the terms that you’ve already set for yourself. Don’t sell her some Potemkin-village version of the kind of relationship you want. Have the courage to openly discuss what you want, respect her enough to tell her the actual terms that would satisfy you, and grant her the room to disagree with you and make an informed decision for herself. Your wife’s experience of this “perfect life” is founded on being constantly lied to. She deserves better.

Help! My Friend Has Been Sharing Photos She Took of Me While I Was in a Coma.
Danny M. Lavery is joined by Hari Kondabolu on this week’s episode of the Dear Prudence podcast.

Dear Prudence,

I’m 20, nonbinary, and about to start hormone replacement therapy. In a few months, I’ll be seeing my entire extended family for a reunion. (I haven’t seen much of them in a few years.) I’m not out to any of them. Because of my history with my parents, I prefer to keep my health care decisions private, although we are reasonably close otherwise. While I know my immediate family is trans-friendly, I really don’t know what to expect from the rest. Is it a terrible idea to stay in the closet and not mention it to anyone at the reunion? By that point I will likely have undergone visible physical change, so they will notice. But maybe if I don’t say anything, no one else will either? I want to get through this gathering with as little awkwardness and conversation around my body as possible.

—Family and Transitioning

It could absolutely go either way. On the one hand, people often fail to notice even somewhat significant physical changes in their family members. It’s not uncommon to have a mental image of a relative from 10 or 30 years ago that is hard to shake. On the other hand, someone might ask you a possibly innocuous but totally closet-shattering question and you find yourself in an uncomfortable situation in front of an audience. (Mine was: “Your skin has been getting a lot worse lately. Did you decide to go on testosterone without telling us?”)

You can politely decline to answer any questions about your body—you know your own temperament best, and if you think you can shrug off any curiosity with relative ease, by all means go for it. Or you can talk to one or two of your relatives you know to be supportive of trans people ahead of time and ask for their help in making sure you don’t have to undergo the third degree, if you decide you don’t want to run the risk of being outed. You can also prepare a stock answer for the kinds of questions you think you might get depending on your flavor of HRT. (Your voice sounds a little rougher lately due to a cold, for example.) You can also dress to minimize whatever HRT’s doing for you (a tight sports bra, binder, or sweatshirt if you’re developing breasts, concealer if you’ve got bad neck acne like I did at first, etc.).

Lots of people start HRT for a few weeks or months (or sometimes longer) before talking to family members about it. So I don’t think it’s a terrible idea to wait to come out only when you feel prepared to do so—it’s a great idea. Everyone should have the space to decide when they’re ready to tell someone they’re on HRT, rather than gauging when they’re going to have to in order to dodge intrusive questions.

Dear Prudence,

I’ve made it a point to try to be friends, or at least friendly, with most of my exes. But those friendships started between relationships, never during one. I recently began seeing a caring and empathetic woman. While it’s still early, I think this could be the start of a good and healthy relationship. The twist: One of my exes just reconnected with me. We broke up more than a year ago, after a few months of dating. Two weeks ago, we met up at a local park to catch up. I didn’t feel any attraction toward them, and it was genuinely enjoyable. I could see reincorporating them into my friend group, particularly because we share a couple of niche interests.

But it’s one thing to introduce a new partner to your friend whom you dated once eight years ago and who is now a platonic friend. It’s another to say, “Hey, we’ve just started dating, but I’m going to start meeting up with my ex for brewery visits and bird photography tours.” My new sorta-girlfriend and I are not at the stage where we’re expecting to be alerted about each other’s social plans. However, I think I would feel insecure and confused to belatedly find out the person I’m seeing has been meeting up with their ex. How can I start this friendship, while also building trust in my new relationship? Is this feasible, or even a good idea?

—Cautiously Friends

I don’t know that choosing your friendships on the basis of whether you might feel insecure if you found out your new sort-of-girlfriend did the same thing is the way to go here. Certainly you don’t have to do anything that makes you feel uncomfortable or that troubles your conscience. But it’s worth investigating that discomfort you feel, because I don’t believe you have duplicitous motives here, nor that it’s inherently risky or romantic to pursue a friendship with someone who shares some of your hobbies and whom you enjoy being around. You and this person dated for a few months over a year ago, so calling them an “ex” strikes me as slightly strong language. You don’t say you two were in love or that the breakup was difficult for you to get over, so I don’t think there’s anything underhanded in rekindling this friendship.

If your new almost-girlfriend considers befriending someone you used to date a breach of trust, that’s probably a sign that she has fairly restrictive expectations for a romantic relationship. Keep getting to know her. Keep spending time with your ex, if you two have a solid platonic connection. If you ever introduce them to each other, you should let your new girlfriend know that you briefly dated your friend Lucinda who’s into bird photography but that’s about the extent of your moral responsibility.

Catch up on this week’s Prudie.

More Advice From How to Do It

A couple years ago—about 10 years into our marriage and amid our trying to fix some desire discrepancy issues—my wife confessed that she cheated on me with a good friend of ours, someone who was in our wedding party and has since made moves on her. This took place about a year before we were engaged, so a long time ago. While we have come a long way, it’s taken me a long time to get over this because of certain details. The biggest of these details is that she told me he performed a particular act for her, one that she enjoyed—an act she won’t let me perform on her. I’m very attracted to my wife; I couldn’t feel like a luckier guy. She is not the most (or least) sexually adventurous person; nor am I. I’m quite happy with our sex life, except that one thing. I’m slightly obsessed with it. She seems to enjoy porn that contains it, and she’s had it and liked it before, but doesn’t want it from me. She claims it’s a hygiene issue, but I feel like that is easy enough to solve. Simply put, I’m not going to do something she says she doesn’t want. At the same time, I really want to shed my insecurity about her getting freaky on the low with our old friend but not me. The male psyche is a little ridiculous, I realize. What should I do?