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FRIENDS AND BENEFITS

I Slept With the Guy Everyone Warns You About

He looked like a cross between Eminem and Jonah Hill, and he carried a Glock. I liked it.

Tootsie Haine

PublishedApr 22, 2026, 10:44 AM EDT

UpdatedApr 22, 2026, 11:04 AM EDT

Updated Apr 22, 2026, 11:04 AM EDTPublished Apr 22, 2026, 10:44 AM 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.

Dylan and I matched on Hinge, but I already knew who he was. We had friends in common, and I’d apparently met him—but not remembered him—at a birthday party.

Born and raised in Los Angeles, he was the son of a well-known events planner. But he’d struck out his own path, into carpentry and construction. He drove a truck.

On our first date, he invited me over for dinner. I slipped into the apartment ungreeted—because he was tending to the baked salmon—and invited myself into the kitchen, clutching a gift: a dusty bottle of red with a picture of Snoop Dogg on the label. At $17.99, it was the most expensive bottle the gas station had to offer.

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He greeted me from the stove with a side-hug. I took him in, in his basketball shorts and slides, and realized I’d been fat-fished. No matter; he looked like a cross between Eminem and Jonah Hill, and I liked how rugged he was.

A roommate appeared shortly after my arrival, just as the fish was getting plated. I raised a brow when Dylan invited him to join us, and a second when he accepted. This man knew whether I was the first or the twenty-first woman Dylan had brought home that month. He knew exactly what I didn’t: just how disposable I was.

Furthermore, because Dylan and the roommate were former classmates and long-term best friends, and the supper-chat theme was growing up in L.A., I had little chance of coming off as a striking conversationalist.

After dinner and sort of to my surprise, the roommate left, leaving Dylan and I to disappear discretely into his bedroom. For conversation, I asked him if he had a gun.

“I have a Glock,” he said. “How could you tell?”

“People have them in L.A.,” I shrugged. “Hotties who look like mountain men do, anyway.”

He went over to his nightstand and opened a small drawer. We peered over and admired the black weapon within. He lifted it out and gently put it in my hands. I kept my finger far from the trigger.

“It isn’t loaded, right?”

“Of course not.”

I stroked the barrel and looked at him until we were kissing. We shed our clothes and were upon each other. He seemed used to lavishing expert oral on a partner. I wondered if it was due to the small size of his penis or the large size of his belly. But when I got on top of him, I realized the gut, fuzzy and massive, was the real secret weapon. My most sensitive parts rubbed against it as I moved atop, giving way to the most immediate orgasm I’d ever had—and my second or third of the night.

I came over again a few weeks later. Dylan was excited by a campfire he had crafted in his backyard. We sat by it and made idle conversation with his neighbor, another long-term, impenetrable friend. I tapped my foot and waited to get laid.

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After the embers died, the passion arose. Dylan and I ate dinner inside and watched Jeopardy! I straddled him on his couch, assuming the combination of buzzer bells and, well, Ken Jennings was sufficiently off-putting to avoid a trivial climax. But later, when we retired to the bedroom, he discovered he’d already come in his pants.

Undeterred, we played on. Our chemistry was so intense that we barely had to touch each other to erupt. I left his house deeply fulfilled and with a fat sense of calm.

Though it had been the “best sex of my life”—and I could finally use that expression without a trace of hyperbole or uncertainty—I didn’t try very hard to cultivate the relationship or even see Dylan again.

(Yes, I had a crush on a friend of his—a stunningly handsome though thoroughly depressed and broken person with whom I had no chance of engaging romantically. Isn’t that always the way?)

It was not until I went on a crucifying date with someone else that the prospect of Dylan—or was it Dylan as a prospect?—seemed desirable and perhaps necessary after all. That same evening, I sent him a voice note saying how funny, smart, and hot I thought he was. Such good (sexual) chemistry was not so common for me, I added.

Some hours later, he responded, saying my message was very sweet and that he felt the same way about me. But he had started dating someone recently, he added. It was already exclusive.

Of course, because he was no longer an option, my heart ached. If I had messaged sooner, I wondered torturously, would things have been different? Or was I always destined to strike out with the night’s daily double?

Tootsie Haine

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