Dear Wendy: “My Boyfriend’s Jealous Of My High School Ex”

After about 1.5 years of dating (four months of it long distance), my boyfriend, Tom, and I have decided to split so we can focus on our careers/degree. I said I was fine with seeing each other when we could and staying in each other’s lives under one condition: that he sees me in his life when he moves back to NY in a year and half. He said he wasn’t sure because, “I’ve always been bothered by who you have slept with before me.” Tom and I are four years apart but attended the same schools growing up, and therefore have a lot of mutual friends/family friends/neighbors, etc. One in particular is John, whom I had a relationship with and slept with when I was 16 years old. We had a dumb high school relationship that lasted all of 4 months. Five years later, John’s brother married Tom’s sister, and now Tom and John are, well, kind of related. This creeps Tom out. I was 16. It was nine years ago. I guess if Tom were once madly in love with my sister-in-law, I could see it being uncomfortable, but a random high school relationship? He told me, that for guys, learning your ex had SEX with a friend of theirs is the equivalent to how a girl feels when she finds out her ex was in LOVE with one of your friends. Is this true? Could it really be such a big deal for him? I didn’t even know Tom when I was with John! I want to make it work for us, but this is just something I can’t change. — Haunted By My Past

I’m sure Tom’s right. For some guys, it’s nearly impossible to get past the idea of their girlfriend having once been intimate with someone they consider a friend or distant family member regardless of how long ago it happened. For other guys, it’s probably no big deal. But it doesn’t matter how other guys may feel, does it? It only matters how Tom feels and if Tom says he’s bothered by the fact that you slept with his sister’s brother-in-law way back in high school, you really have no choice but to believe him, and since you certainly can’t change the past, I’d recommend moving on.

You both laid your cards on the table and your hands don’t match, anyway. You’ve already decided to split up; neither one of you is invested in the relationship enough to commit through the next year and a half of long-distance. You only want to remain in contact with him if he sees a future with you; he says he’s not sure he does. End of story. That’s all you need to know. Frankly, if you both saw a future with one another, you wouldn’t be splitting up. You’d make staying together and working through the distance as much a priority as your careers and degrees. If you truly wanted to “make it work,” like you say you do, you’d make it work now, not a year and half down the road. Obviously, there’s not enough between you to make the kinds of sacrifices you think are necessary, and that’s fine — hey, better you admit that now than after years of trying and failing.

I think the answer to all your questions about this relationship lies in the very first sentence of your letter: after a year and half of dating, you’ve decided to split up. Anything after that is pretty inconsequential. You’ve decided to split up. That means there’s no relationship — or at least not enough of a commitment to make one work. If you’d begun the letter by saying that after a year and half of dating, you’re ready to make a deeper commitment, but Tom’s insecurity about a relationship you had when you were 16 is the only wrinkle,” I might have some different advice for you. But you didn’t start your letter that way. You started with a declaration that you’d broken up. You want my advice? Stay broken up.

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