Sexplain It: I Keep Dating ‘Straight’ Guys Who Cheat on Me With Other Men

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I’m Zachary Zane, a sex writer, author, and ethical manwhore (a fancy way of saying I sleep with a lot of people, and I’m very, very open about it). Over the years, I’ve had my fair share of sexual experiences, dating and sleeping with hundreds of people of all genders and orientations. In doing so, I’ve learned a thing or two about navigating issues in the bedroom (and a bunch of other places, TBH). I’m here to answer your most pressing sex questions with thorough, actionable advice that isn’t just “communicate with your partner” because you know that already. Ask me anything—literally, anything—and I will gladly Sexplain It.

To submit a question for a future column, fill out this form.

Dear Sexplain It,

I am a straight, cisgender woman who just ended a third relationship in a row where the guy I’m dating is fucking other men in secret. These men all claimed to be straight, and we did not have an open relationship. I’m not against men fucking men, but when it’s cheating, it’s cheating, especially when it’s random hookups on Grindr. Why does this keep happening to me?

—Accidental Beard


Dear Accidental Beard,

You know what they say: twice is a coincidence; three times is a pattern. This doesn’t “keep happening” to you randomly. I think there must be certain characteristics in these closeted queer men that you’re attracted to.

Could it be that you’re drawn to men who aren’t interested in you? Some people who who pine and chase after unavailable partners are acting from a place of insecurity and low self-esteem, the (misguided) idea being that if the unavailable partner finally does commit, the chaser will have proof that they are worthy of love.

“I have seen this quite a bit in my practice over the years,” says Joe Kort, Ph.D., LMSW, certified sex therapist and director of The Center for Relationship and Sexual Health. “Women are attracted to the unavailability of the man because his attention is elsewhere, but she doesn’t have anything concrete to pinpoint until she discovers he has broken the agreement and has cheated.”

Sound like you? Talking to a therapist can help you unpack (and challenge) the core insecurities driving you toward unavailable men. And in the meantime, I recommend you read Attached: Are you Anxious, Avoidant or Secure? How the science of adult attachment can help you find–and keep–love to learn more about your (likely) anxious attachment style.

If that doesn’t sound like you, I wonder if you’re attracted to closeted queer men for an entirely different reason: Many don’t abide by heteronormative scripts when it comes to dating and love, instead opting for a more egalitarian relationship.

“I’ve noticed in my practice that gay and bi men often treat women really well,” Kort says, adding that they’re more likely to share the housework, more open to communication, and less likely to be possessive. These are wonderful qualities to seek in a partner—but you need to find them in someone who also isn’t going to cheat on you. These guys do exist!

The next guy you date, I would make it very clear early-on the type of relationship you’re looking for, instead of assuming the guy will operate the exact way you had in mind. It is not weird to ask a guy on a dating app, even before you meet up, “What do you look for in a relationship? What do you look for in a partner?” Or, if you prefer, you can ask this on your first date. It’s not “too soon” to ask. You’re simply trying to ensure you’re on the same page; otherwise, you’re wasting each other’s time.

When you have this convo, explain how you want a more egalitarian relationship and how monogamy is something that you value. I’d also share how the last three men you dated cheated on you, so you’re having some issues trusting men.

Did you discuss being monogamous with the last guys you dated? Or did you simply assume they were being monogamous because you had been dating for a while? Never assume anything. For one, your partner isn’t a mind reader. Two, some folks, often men, revel in the unsaid. They justify their unethical behavior with dubious logic: “Since we never said anything outright, even though it was very, very implied, I technically didn’t do anything wrong!”

Since you don’t want that nonsense, communicate your wants, expectations, and what you’re seeking from a partner clearly from the beginning.

Accidental Beard, I cannot guarantee that the next man you date won’t cheat on you. However, I do believe that if you work on your insecurities, better understand your attachment style, state your boundaries, and clearly express your expectations, there’s a much better chance your next boyfriend will respect your choice to be monogamous together.

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