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FRIENDS AND BENEFITS

Why I Regret Sleeping With My Ex in Las Vegas

Our encounter reminded me of something my brother once said: getting a hotel room is a waste if you don’t have sex in it.

Tootsie Haine

PublishedApr 29, 2026, 12:03 PM EDT

UpdatedApr 29, 2026, 2:51 PM EDT

Updated Apr 29, 2026, 2:51 PM EDTPublished Apr 29, 2026, 12:03 PM EDT

Welcome to Friends and Benefits. Follow our new sex and relationships columnist into the lives and psyches of men and women, young and old, gorgeous and tragic, divine and insane. All names and identifying details have been changed to protect the privacy of the bachelors in question.

When I was 19 and on a gap year working at a production company in Los Angeles, I lived in a trailer I found on Craigslist: a silver Airstream with a brown carpet, foam bed, a defunct kitchen, and an ornamental bathroom.

The trailer sat in the yard of a large warehouse, which was home to about 14 people. Their ages ranged from 18 to 55 and they worked in industries as diverse as photography, webcamming, food delivery, and motorcycle repair.

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Kyle was one such occupant. He was 30-something and covered in tattoos. (On one occasion, he had asked an artist for something small and dangerous, he told me, and was given a syringe on one arm and a grenade on the other.) That was all I needed.

We would go on excursions: taco trucks, museums, IKEA, a screening of Fight Club on the Fox studio lot. He told me people said he looked like Edward Norton—and I told him I always preferred an Ed to a Brad.

He was given up for adoption by his teen mom in Rhode Island, he told me. He had been something of a delinquent in high school, barely graduating and going to community college 10 years later. I bit him on the lip and said that I loved his style.

On a day we had a hangout planned, I texted Kyle and asked when he was free. He didn’t respond, but later posted a video on Instagram of a keyboard issuing a sullen beat, with a caption that his day off had been well spent. He eventually sent a paltry query about doing something over the weekend instead.

With the guidance of a friend who took no crap, I texted him to ask whether our relationship deserved more emotional investment. He didn’t respond. And that was that. Until it wasn’t.

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I went back to New York and kept lazy social media tabs on him. At some point he got a girlfriend. She was blonde and chubby. Her appearance inspired a poll among my friends: Is it more upsetting to see your ex with a bombshell or someone you find surprisingly unattractive? Most people said bombshell, but I thought the latter was worse.

If the reasons for which an ex—or indeed anyone, but especially an ex—likes their new person are intangible, it must mean their connection is intense.

Six years later, Kyle messaged me out of the blue and asked if I would like him to return a book I had given him. He was moving to Las Vegas and consolidating. I said sure, and we kept talking.

I informed him that I would seen be in Sin City myself for, of all things, a baby shower, and asked if he would like to hang out. His reaction was extremely enthusiastic.

We met at a casino. He was shorter and nerdier-looking than I remembered. He told me he and his girlfriend had been in Vegas for a while now, but he had his sights set on returning to L.A. We went to a tiki bar and got very drunk.

I thought about something my brother had once said: that getting a hotel room is a waste if you don’t have sex in it.

Kyle and I made out at the bar and went back to the room. From what I could remember, the passion was surprising, and after he left, I walked across the road and bought a $26 chicken sandwich at the Bellagio.

I had hooked up with people again after a long intermission before and had found it a sort of nice tradition, but this time, despite the passion, it had been depressing. The compulsion to revisit an old flame can disturb the image of it; the memory loses its glamour.

Months later, Kyle somehow sensed that I had moved back to L.A. myself. In between posting collages for his girlfriend’s birthday, he messaged me on Instagram about getting together. I was vague.

It would have been too easy not to reply, but I—unlike Kyle—find that giving someone something, even a few words, however negative or inconsequential, is superior to silence.

Maybe it isn’t helpful or sexy or altruistic, but I can’t help it. And so, when he texted me to suggest hanging out, I responded in kind—or not-so-kind: “I don’t know what I want, and I’m not sure you do either.”

Another two years later, and days before I was set to leave Los Angeles again, Kyle texted me.

“Hey. I don’t know if you’re in L.A., or if you’re single, but I would love to see you sometime,” the message read.

I didn’t end up seeing him. Still, you never know—from the moment you have met someone, if the connection was strong at any point, the door is open, and likely to remain so. For me, closure does not exist. Nor should it.

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Tootsie Haine

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