Ask Damon: Should I date someone who was mean to me in college?

Hi Damon: Is dating someone who was kind of mean to you a smart idea? Context: We went to the same college together +10 years ago and had mutual friends. This guy and another friend of his were mean but sometimes chill, and he gave me a ride home from the grocery store (one time … lol). He did call me a very mean name, and I can’t let it go. What are your thoughts? Thank you!

Should I?: I am probably not the best person to answer this question, because I bind onto an old grudge like a wet tongue on dry ice. I still wish broken shoelaces and sticky shower curtains on people who cut me in lunch lines in middle school. I don’t particularly enjoy conflict, but the ceaseless possession of simmering grudges keeps my teeth white, and I’d rather date a dead gnat than someone who was unkind to me in college. But you did not ask “the best person” for advice — you asked me! So let’s get rolling.

Actually, let’s stop rolling. Without more context from you, I don’t know if I can answer this without a DeLorean and a drone. “Mean” can mean so many things, because the spectrum of what constitutes meanness is arbitrary and limitless. Let’s say, for instance, that he teased you for wearing neon pink socks with medium blue shoes, and started calling you “SK” — short for “sentient kaleidoscope.” To a self-conscious 20-year-old, hearing this from someone you might have had a crush on could’ve felt mean. Even meaner if he knew you liked him. I wouldn’t consider it unforgivable, though.

But then let’s say he was dissatisfied with your relationship, and then he faked his own kidnapping and murder just so you’d be charged with it. (And then, on a whim, killed Doogie Howser!) Yes, this is the premise of Gone Girl. It is also unforgivably mean.

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Wait, I was wrong. I can answer this! It doesn’t matter if I consider the meanness to be unforgivable, or where it falls on the spectrum of mean. What matters is that, a decade later, you’re still bothered by it, which means it was hurtful enough for the wound to still smart. And you know what? I’m not going to tell you to get over it. I mean, I think you should, for your own sake and on your own time. But I don’t think it’s a great idea to fast track your healing just so you can date the man who caused the hurt. A better idea? Maybe get a pen and some paper, write down the names of all the men who have been mean to you before, and then … don’t date them. You don’t even need to accept rides from them anymore. Just Uber.

Also, I’m curious why you’re even entertaining this. There are many unflattering characteristics a person can have. Most can be explained, excused, or ignored if you squint hard enough. When a person reveals a habit of meanness — particularly when they’re mean to people who have less status and power than them — that should be the reddest possible flag. And not just with romance, but in any interpersonal relationship. Let me ask — would you be friends with this guy if you weren’t interested in dating him?

(And I may have read your letter too quickly, but I didn’t see any mention of an apology from him. Let me reread it. Yup. No mention.)

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