I’m Zachary Zane, a sex writer 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,
My best guy friend, Joe, has been with this girlfriend for two years, and he told me he’s about to propose. (Both his own family and girlfriend have really been pressuring him to get engaged.) I like his girlfriend, and recently, we saw a movie together because we have similar tastes. I can see us becoming close friends, independent of him.
But I’m worried that this will put me in a weird situation because Joe cheats on her. I’ve seen him shamelessly flirt with women at bars, and he’s told me that he cheats on her when he’s out of town for work. From what it seems like, his girlfriend is oblivious to everything since, when he’s with her, he’s on good behavior.
I’ve told him he should stop or talk to his girlfriend about an open relationship, but when I throw out these ideas, he immediately dismisses me. Since I now have an independent relationship with his girlfriend, I feel like a bad friend not letting her know that he cheats. I never thought I would tell her, but with Joe about to propose, I feel like if there was a time, it would be now. What should I do?
— Bad Friend
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Dear Bad Friend,
I think Joe’s fiancée needs to know about the cheating, but don’t go straight to her. First, talk to Joe. Let him know that if he doesn’t confess to his infidelity, you’re going to tell her about it. Joe will be pissed, and will likely attempt to invoke some form of “bro code.” He might call you a bad friend, but you’re no the bad friend here. Joe is. He’s put you in the extremely uncomfortable position of having to decide between your friend and your morals. Not to mention he’s being an asshole by constantly cheating on his girlfriend.
While you might be worried this isn’t any of your business, it became your business when Joe told you about his repeated acts of infidelity. For what it’s worth, I wouldn’t be giving the same advice if he had cheated once while drunk, felt terrible about it, and has never cheated since then. In that situation, I’d tell you to shut your damn mouth. But that’s not what happened. He is repeatedly choosing to break his partner’s trust and lie to her. Clearly, he doesn’t respect her—or you, given that he’s totally fine burdening you with these secrets. So, frankly, I believe he is a friend worth losing.
Besides, I don’t think you’d be able to have a real relationship with Joe and his fiancée if you didn’t say anything. You’d have guilt eating at you, so, realistically, you’d probably stop being friends with both of them. At least when you tell them, you can sleep at night knowing you made the ethical decision that aligns with your morals.
As for how to tell Joe? Sit him down and let him know you have something serious you’d like to talk about, then say something along these lines: “Joe, I feel as if I’ve been put in a real dilemma. While I don’t want to break your trust, I feel really uncomfortable knowing that you’re going to marry someone and have and are continuing to sleep with other people. I don’t think it’s fair to her. If you really do want to marry her, you should stop cheating and tell her about your past indiscretions, so you can work through it.”
If that sounds terrifying, here’s a bit of slightly encouraging news: When I showed your question to Megan Fleming, Ph.D., a sex and relationship expert for Lovehoney, she said there’s a chance your intervention could lead to a stronger relationship between Joe and his fiancée. “If [Joe] chooses to do the hard thing and tell his girlfriend, they can [potentially] choose to work on rebuilding the relationship and re-negotiate their relationship structure,” Fleming says. “I’ve had many clients successfully repair from the pain of infidelity and find solutions that work for both partners, including that sex is okay if out of the country on business.” Or, they may call off their marriage, which could also make them happier in the long run.
Unfortunately, I’m guessing there’s a good chance Joe will refuse to come clean to his fiancée, leaving the ball in your court. When you talk to her, you don’t need to go into details about everything Joe has done. It can be simple as: “I think you need to talk to Joe. I’m sorry to tell you that he hasn’t been faithful to you, and I felt it was important for you to know this before you choose to marry him.” Hopefully, she doesn’t shoot the messenger.
Bad Friend, this whole situation really sucks. That’s just the simplest and most accurate way to describe your predicament. You should not have to be in this position, but hey, it might not all be bad. While you may lose Joe as a friend, it can be the start of a friendship with his fiancée.
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