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FRIENDS AND BENEFITS

My Only Regret About Taking a Road Trip With a Man I Barely Knew

I drove cross-country with a near-stranger, and all I got was this stupid existential crisis.

Tootsie Haine

PublishedMay 20, 2026, 5:18 PM EDT

UpdatedMay 20, 2026, 5:19 PM EDT

Updated May 20, 2026, 5:19 PM EDTPublished May 20, 2026, 5:18 PM EDT

Welcome to Friends and Benefits. Follow our 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.

This is the second half of a two-part series. First, read The Road Trip: Part I.

Day Three: Amarillo to Memphis, by way of Oklahoma City

Wes—yes, we were now on a nickname basis—and I split a dynamite Texas-shaped waffle for breakfast at a Best Western in Amarillo, en-route to the charmless Oklahoma City and a lunch at Raising Cane’s.

Over the greasy crunch of chicken tenders, we talked about tattoos. (Neither of us had any.) Back in the car, I dug out a pirate-themed temporary pack. Wes went for the arm; I went for the neck.

Perhaps buoyed by that rebellious body art, we had a hot make-out at a rural gas station. As we left, an elderly, slow-moving woman in the bathroom touched the shoulder of the small restroom attendant and said, “You have a thankless job, so I’m going to thank you.” We drove on.

Minutes outside of Memphis, I booked us a room at the Peabody; the lobby looked massive and glitzy, and there were purported to be loose ducks in the fountain, but we didn’t see any.

Our room was small and shaped in a way that made it feel ersatz. We lay on the bed and talked about recent romances, sex, and why he couldn’t have it, and the carnal tragedy of Lexapro.

I had never been on Lexapro or any other SSRI, but it seemed that the proliferation of mood stabilizers and antidepressants had made a mark on our generation, suspending users from despair—and from physical intimacy. To me, sex had always felt like a life force, the anti-death. I mourned the loss.

I changed into my pinafore, and we hit the Blues City Cafe for ribs. Dessert was more ketamine in the bathroom. We paid $5 and went through security to get to Beale Street. The smell of Memphis! The heat in the night air! Rowdy groups of people ran up and down the street, but every place was almost empty.

Wes said that a heightened police presence—metal detectors and security personnel instated in an attempt to quell criminal activity and perhaps liveliness itself—meant that there were fewer performers operating on the street.

In such a protected pen, we were free to take on the role ourselves.

Day Four: Memphis to Christiansburg, Virginia, by way of Nashville

A whole day spent driving through Tennessee. Passing the time, I read Wes interviews and excerpts by writers I liked. He told me about a short story he wrote in college, and I read that aloud, too. He was embarrassed, and privately I thought it was bad.

We talked about motorcycles. We talked about ambition, of the people we had seen across the country—was it good or bad that they didn’t seem to have any? (And what about us?)

He talked about his parents’ divorce. I asked him when he lost his virginity; he told me about the girl in college who squirted and soaked his bed. Wes wasn’t sure he’d ever been in love. I thought about our trip and whether we were at all close to it, or could ever be.

We stopped for Dunkin’ Donuts and a toilet break, and we made out again. He said he didn’t have to pee anymore and we got back in the car. “Can I see your dick?” I asked. (Finally, some action; you have to seize it.) I went down on him, crushing a banana under my cowboy boot heel in the frenzy. Some tweens outside the store sensed something was comical, and laughed at us.

Day Five: Christiansburg to New York City

“Tongues aren’t for the morning,” Wes said as I kissed him in our room at a Holiday Inn.

Our last night on the road was over. I was grieving the intimacy we never managed, while savoring the companionship and tenderness we had found.

As Wes drove with patience and concentration, I fondled his earlobe. Wes had done almost all of the driving. He liked it, and it suited me. He had gotten me across the country, and that’s what I needed. Maybe that was good enough.

Maybe it was more. I kept looking over at him, and found myself smiling involuntarily. I loved to look at him, I couldn’t stop. Awe, gratitude, and pleasure. He’d sense my smile and look back—not the same look, more receptive. Who knew exactly what we meant to each other? And what should we have meant to each other?

There were complicated things in him, in me, and between us. He was able to voice some of them, able to convey something of how he felt within himself, and about me. But was I receptive? Did we ever believe at any point that we were made for each other? Or was it just that we got on?

I thought about his bad short story. I didn’t really think I could ever love someone whose work I didn’t respect, but I could certainly still have the hots for them.

After the Trip

I was excited by the return to my closest friends in New York City, and wanted to see them, but not yet, and not only. I wanted what was new; I felt as if life on the road was life lived, and what comes after is life recounted.

I regretted that Wes and I hadn’t hooked up, had sex, made love, whatever it would have been. I wanted to be as close to him as possible. I missed him.

At that very moment, he texted me: “Should we drive back?”

A few days later, I collected Wes—not for the road but the airport. We were relieved to be back in the car and in each other’s company. We held hands. I told him that the trip had communicated something to me, something I didn’t yet understand. I felt a premature nostalgia.

Over dinner later that night with family friends in the old neighborhood, I ate and didn’t talk, glazed over the gossip, and thought about him.

I did see Wes again, about six months later, for a quick lunch when he was in the city visiting family. I was struck by emotion. We had been through something very intimate, after all.

The lunch was followed by two others (and a few postcards) over the next several months, but by then the meetings were short and about work. We were still fond of each other, still close, but something had faltered, and I doubt it will ever return.

Got a question about dating, an opinion on intimacy, or a comment about Tootsie’s tales? Share your thoughts with our dating columnist at tootsie.haine@thedailybeast.com.

Tootsie Haine

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