I’ve cheated with my ex from high school


They’ve been together now since 2015 and have more kids. I still hear from him at least once, sometimes three times, a year, and have met up maybe four times and have even had sex those times. He tells me he isn’t happy, misses me, wishes he never left me, and that he and my ex-friend will never have what we had. He tells me he checks my social media at least once a week.

If he feels this way, why doesn’t he leave her? Does he really love me if he says these things but won’t leave? He always says he doesn’t want to have to be taken away from his kids, which I understand.

Recently I started dating more — for the first time in 10 years. Mostly, I didn’t think about my ex at all. But then as experiences fade, I find myself missing him, and recently linked up with him. What can I do on my end to forget about him? What is my ex’s motive for all of this reaching out and telling me his secrets and deepest feelings? When we dated he was super prideful and would never admit to any feelings, and acted as if I was not able to affect him. Today he takes full responsibility for what he’s done and is remorseful, but why now?


A. “What is my ex’s motive for all of this reaching out?”

Possible answers:

1. He needs attention. 2. He’s bored. 3. He wants a mini-vacation from his partner and children. 4. You remind him of an easier time (high school). 5. He likes to manipulate people. 6. He’s lining up a backup partner, just in case things go wrong. 7. His actual partner doesn’t have time to focus on him much because of the kids, and he knows you’ll listen (this one is similar to No. 1, I guess).

Notice that nothing on that list is about you. He’s not fueled by selfless love or a real understanding of what he left behind. You were with him as a teen, which means he barely knows you now.

Also, when he’s with you, he’s talking about himself. He might love the way you make him feel, but he’s not focused on making you happy.

You’d be happier with a love that’s yours, one that doesn’t require waiting, decoding, lying, and second-guessing. He can’t give you that, and his remorse, while nice to hear about, has nothing to do with what he can offer now.

You said that when you were dating others you didn’t think about him that much. Maybe that means you should get out there more. Not just with dates, but with friends. Embrace the part of your life that has nothing to do with him.

It’s easy to make this situation sound romantic — to say that you were soul mates in high school, that you were pulled apart, that you never forgot each other. But the reality is, he’s just some person cheating on his partner after a long history of toxic behavior.

Cut him out. Instead of asking, “Why now?” consider, “Why should I care?”



Stop it. I understand if you want to get even with your ex-bestie from a decade ago, but this guy has children.


The real question you should ask is why are you still involved with him? It’s a two-way sleazy street here. He’s cheating on her with you whether they’re married or not. You’re an active, willing participant. If you’re hoping he’ll leave his family for you, you deserve him. And ultimately he’ll cheat on you as well. Neither of you have matured since you were teenagers.


“My high school boyfriend and I had a passionate but toxic relationship.” Whispers: it’s still toxic.


Send your own relationship and dating questions to [email protected] or fill out this form. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.

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