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How I Stopped Being So Jealous of My Wife's Cool Exes

I couldn’t stand that my partner’s ex-boyfriends were so effortlessly awesome … until this happened

Photos of people in photo frames with hand drawn doodles over the faces
Paul Spella and Hendrick Onderdonk/iStock

When my wife and I first met in our 20s, there was a striking difference between us. Cassandra was cool, whereas I was nervous about drugs, bars, clubs, motorcycles, eating alone at a restaurant and excessive cursing. 

Dating a cool woman was exciting. But it had a serious downside — all the guys she’d dated before me were cool. I’d hear stories about them and feel a version of emasculation that was like seeing a motorcycle zip by when you’re on a Huffy.

I was intimidated by all of them: three painters, two drummers, a theater director and a bartender who sold cocaine.

We’re middle-aged parents now, so cool shouldn’t matter. Except it does. Because while most cool guys leave their glory days in their youth to become suburban sales reps, these guys all became successful at their cool professions. They’re somehow cooler now. 

I’ve done fine in my career, but not in a cool way. The best I get is people saying, “My parents loved your Time column.” And the people saying that are older than me. 

When I Wikipedia her boyfriends, I feel lame. Cassandra’s college boyfriend was Michael Counts, who has a Wikipedia page way longer than mine. It notes that he was called a “mad genius” and “a master of immersive theatre” by The New York Times, whereas my page mentions that Vanity Fair called me “a forgettable I Love the ’80s participant and Time magazine humor (?) columnist.” 

When we started dating, Cassandra often wore a leather motorcycle racing jacket she was given by a boyfriend, a divorced artist 12 years older than she was. According to a lot of Google image searching, he now has long hair, sometimes wears a cowboy hat, makes stuff out of neon and has shown his work at the Venice Biennale. I can’t even pull off a cowboy hat.

When Cassandra slept over in the Manhattan apartment I shared with two roommates, she would look up groggily in the morning to stare in wonder as I got dressed. But not in a good way. 

“You put on a pair of khakis and a button-up shirt every day,” she says. “I’d never dated anybody before who put on normal adult male outfits.”

The first few times I put music on in my room, she was equally confused. “When you told me you liked the Counting Crows and Hanson, I thought you were doing some post-ironic bit,” she says. “I couldn’t believe how little you cared about being cool.”

She might be comfortable with me, but she missed out on a cool husband. A life with some edge in it.

I was silently stewing about this recently when we were walking around her college town, Saratoga Springs, New York, with our son. She was pointing out every bar she hung out in. We went down a residential street when we saw a guy about our age on a bicycle coming down the block. 

“I used to date that guy,” she said. It was one of the drummers.

He must not have noticed us because as he was riding by, he popped a wheelie. 

A 40-something adult man who slept with my wife on multiple occasions popped a wheelie

It was as if the entire burden of my uncool, non-drug-taking, non-drum-playing existence was lifted off my J. Crewed shoulders. Not all at once, but over many months as I kept saying to my wife things like, “I might be late coming back from the pitch meeting, depending on how many times I pop a wheelie.”

Now all I have to do is find one hugely embarrassing thing about each of the other guys she dated. I don’t expect every one of them to TikTok their wheelies. But I’m going to keep looking until I find something close.