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

















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