Ask Him: My Boyfriend Cheated On His Last Girlfriend

Q: “I’ve recently started dating a guy, and we’re starting to get more and more serious. We share some mutual friends, and they have told me that his last relationship ended because he cheated on his girlfriend and she found out. Now I’m worried about him cheating on me. What should I do? Talk to him about it? Run away screaming? Please advise.”


A: Since a girlfriend cheated on me more than half a decade ago, I have been very wary of people who have cheated on past significant others. Maybe too wary. I feel like I certainly haven’t given a few people the benefit of the doubt when I probably should have. My first instinct is to steer completely clear of anyone with a history of cheating. (But I also already have deep trust issues. From, you know, being cheated on and all.) There was even one time where a woman cheated on her boyfriend with me, and one of the main factors of our not getting more serious once she broke up with him was that I was too afraid she would eventually bout-face and do the same thing to me that she had done to him.

It’s very, very difficult to shake the negative thoughts that come when you find out your current boyfriend has cheated on another woman in the past. I bet that when you initially heard of this, it felt like you had just been punched in the stomach after consuming a bad batch of egg foo young. There’s good reason for this, obviously, and you’re totally right and justified to tread lightly. When you enter a relationship, you don’t want to become a victim of a recurring negative circumstance or circumstances that were toxic to a former relationship, and cheating is at the highest and darkest peak of such negatives. (Aside from physical abuse, I suppose.)

A few years ago, I would’ve told you to run; run away, and never return, probably in a voice impression of Scar from The Lion King. I would have told you to not even bring it up with him until the break-up conversation.

But I’ve come to realize that sometimes people make mistakes that they learn from, and that just because a person does something one time doesn’t mean they’re going to do it again. (I mean, do you think Jonah Hill will ever call a paparazzo a f**got ever again?) I’ve also learned that people grow and mature. Their personalities change, and so do their morals. And so do the actions they take.

So you should at least talk with your boyfriend about it. This isn’t going to be a joyous conversation (at least from the start), but if he gets upset, remind him that you’re talking to him civilly about a terrible wrong he committed that probably hurt another human being very deeply.

If he tries to tell you it’s in the past, like the number of sexual partners the two of you have had, acknowledge that this is correct, but that unlike sexual partners (assuming the two of you have been tested recently), this is an issue that you fear may eventually have implications on your own relationship.*

If you hit this point and he is still totally unwilling to discuss his philandering with you, then you should hit the road. You know what Paul Rudd’s character in Forgetting Sarah Marshall says: “When life gives me lemons, I say f**k the lemons and bail.”

But if your boyfriend is open about his past transgressions, hear him out, and then decide for yourself if you truly believe he will or will not cheat on you.

There’s no perfect way to about making this decision. It’s a judgment call. I hope you end up making the right choice.

*A clarification: If you and your boyfriend are both proven to be STD-free (and if you’ve both gotten all three rounds of the Gardasil vaccination), it shouldn’t matter all that much how many people you’ve copulated with in your previous life—which is to say your life before you met your current main squeeze. However, the number of people you have slept with while in an exclusive relationship with another human being is of the utmost importance.

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