Lifestyle

FRIENDS AND BENEFITS

He Was Rich, Rude, and Weirdly Unforgettable

My aunt told me to be the artist in the relationship. Lawyers, financiers, and blue-bloods were abundant, after all.

Tootsie Haine

PublishedApr 15, 2026, 2:40 PM EDT

UpdatedApr 15, 2026, 3:14 PM EDT

Updated Apr 15, 2026, 3:14 PM EDTPublished Apr 15, 2026, 2:40 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.

“Actually, a lot of the assholes I know are gentlemen. Or vice versa. Dickheads with a family crest and a prep-school code of honor.” —Jay McInerney, Story of My Life

I was 27. I had quit my corporate job and moved in with my aunt in New York. She wasn’t in town much anyway. I started writing all day. I made no money. I didn’t have a boyfriend.

I was still young, but not so young as to ignore the fact that it was time to get out there and find a romantic patron. My aunt told me to be the artist in the relationship. Lawyers, financiers, and blue-bloods were abundant, after all.

I met Quin at a dinner party in the Hamptons. The cousin of a good friend, he was also 27, basketball-player tall, and heir to a baby food fortune. We traded looks and commentary from across the table. When I told him I was throwing a bonfire with my friends later that night, he opted to join.

A week or so later, we had a drink in Manhattan. He was sweet and seemed eager. We talked about our mutual dislike of tattoos; he said he hated fat people, or at least blamed them for their size. I shrugged it off, eyes on the prize.

We took a walk around Central Park. He told me that he never made the first move, or any move, but was very receptive. So I kissed him.

Back in his apartment later, he traced my upper lip with his finger, exploring the peach fuzz.

“Is it a choice?” he asked.

“Are you trying to make me insecure?”

“No, I’m not teasing you. I was just wondering.”

“Well, I do clear it away from time to time.”

We made out until past three in the morning, but he did not grope me—a pleasant surprise. He then asked me how I was getting home, but didn’t offer to call a ride for me. I wouldn’t have accepted one anyway.

The next weekend, I went straight to his place after a visit with college friends upstate. I told him it had been a tattoo convention. He laughed, but later asked me if I thought women were funny.

“Funny in the Amy Poehler, women of Saturday Night Live sense? Or funny in the Hitchens sense, like they don’t have to be?”

“Answer the question. Are women funny?”

“Of course. There are four billion women in the world. It would be foolish to make such a generalization.”

He said he supposed I was right about that, but went on as if I weren’t: Something about the intrinsic humor in men and a man’s role in society. We talked about shame, humiliation, and stand-up comedians.

(Incidentally, I often find that the men I’m on dates with are starkly unfunny. Being funny is rare.)

I noticed a Trump 2024 mailer on the table, but said nothing. Instead, I followed him into his room. We kissed and petted.

“I like your touch,” I said.

“It’s probably my best quality,” he said. “My least evil.” He laughed a bit.

“Last time you were here was the longest kiss I’ve ever had without tongue.”

“What?”

“Sans tongue.”

“Huh?”

“Your jaw was shut.”

“No way!” I said. “I have felt tongues in my life, surely....”

If Quin’s wish was to stump me or make me self-conscious, I don’t recall whether or not he was visibly pleased by his success. But after the micro-lecture, we were back in each other’s mouths, tongues salient.

By that point, I was sure that Quin and I were not meant to be. Still, I couldn’t bring myself to, well, make the first move. I couldn’t bear a hard out, a firm ending. So five days later, I was offering him a lift out to the Hamptons for no particular occasion—at least beyond the prospect of a final weekend tryst.

I picked him up from his apartment. He bounded into the car, and rubbed a massive stye on his eyelid. He had alerted me to it the last time I was over, not that I would or could have missed it; I’d said nothing but that it was no bother. Direct insults weren’t my style, but since they were his, I’d been inspired to think up a few unfavorable comparisons: Ichabod Crane from Disney’s Sleepy Hollow; the Scarecrow from The Wizard of Oz.

On the three-hour-long drive, I realized that Quin was evil and boring. We spoke little, and about nothing. I didn’t try because I no longer cared. Manners vanished—he left me to pump gas as he stood outside the convenience store, demolishing a CLIF bar.

I dropped him off at a relative’s house on the beach. He gave me a quick kiss. I told him I would be around—I had gotten a wax for the occasion and didn’t want to waste it.

I texted him at 11 p.m. that night to see if he wanted to go “for a drive.” He texted back immediately—he was at the club, and asked if I wanted to rescue him. I was miffed that I hadn’t been invited, so I left him on read; he told me he was going to walk home.

“Why are you even entertaining him?” the friend I was staying with asked.

“The inability to look away from a car crash,” I replied.

And with that, I texted an offer to go to the beach for 15 minutes—sit on a lifeguard chair, take it in… (The implication was clear.) His response: “OK, goodnight.”

“You don’t want a ride or the chair?”

“I just don’t want to go to the beach.”

His texts continued, an artless and actively disengaging stream-of-consciousness:

“I am actively walking home.”

“In the dark.”

“Very peaceful.”

“The moon is large and in half.”

I had to stop him: “Need a ride or nah?”

“I can probably make it... I’m pretty drunk.”

“Just let me know if you might need a collection… I wouldn’t want you to get mowed down.”

“I’ve been avoided thus far,” he replied. “You’re more than welcome to come join me. But I’m just going to bed down.”

“I’m going to bed now, too, but I did want to be quiet and touch.”

“Well...the offer is the offer.”

The offer was the offer. It was 1:15 a.m. A sick part of me wanted to take him on, but was overridden by the reluctant knowledge that such a move so obviously lacked self-respect.

I wasn’t above digging for attention, but I was far past the opportunity of marrying into money—and now I couldn’t even have sex with the guy. I went to bed alone.

Tootsie Haine

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