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FRIENDS & BENEFITS

Why I Asked My Handsome Coworker on a Cross-Country Road Trip

We barely knew each other. That didn’t stop us from taking ketamine and kissing our way across Interstate 40.

Tootsie Haine

PublishedMay 14, 2026, 10:59 AM EDT

UpdatedMay 14, 2026, 1:07 PM EDT

Updated May 14, 2026, 1:07 PM EDTPublished May 14, 2026, 10:59 AM 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.

I had decided to quit my job, give up my apartment in Los Angeles, and move back to New York City. I was too much of a hoarder to fly; I’d have to stuff my car and drive it cross-country. My mother told me not to make the drive alone. Go with a man, she suggested.

I didn’t think she understood. What use was a man going to be these days? Were they still versed in the art of protection? The few guys I knew in L.A. who had guns were not available. I told my mom this, and she said any shrimp would do. But none of my other male friends could go, or seemed truly up for it. (And truth be told, I didn’t particularly want to travel for that length with anyone I already knew.)

After I gave my two weeks’ notice to the talent agency where I’d posed as a secretary for the past year, I was tasked with helping to find my replacement. That’s how I met Wesley, a good-looking guy from the agency’s music department. He wore corduroy to the interview and didn’t get the job. Still, we hit it off at once. We had lunch.

A week later, I texted him: “I have a proposition for you. When are you free?”

We met for a walk that night, and I asked him if he would consider joining me on my drive across the country. He couldn’t believe I wanted him. I told him it was intuition; I sensed he might be willing, and that willingness is rare. I quoted Bret Easton Ellis: “People are afraid to merge.”

He asked me if we’d have sex on the trip, and then apologized for being blunt. I was thrilled, but tried to be coy.

“We should retain a little mystery, but I understand what I am asking of you, to come all that way,” I said. “Of course, if it’s what you want, I’ll certainly put out.”

The next day, he wrote me: “I’m in.”

Day One: L.A. to Flagstaff, Arizona by way of Las Vegas

I picked Wesley up at 6:30 a.m. on May 1.

Our first pit-stop set the trip’s tone: He hadn’t been to Vegas since he was 12, and wanted to gamble. We hit the tables at the Wynn Hotel and Casino later that morning. I watched as he ran through some $200. He was a good loser.

We drove on. Interstate 40 was the idea. During a break in Kingman, Arizona, Wesley loaned his phone and gave a cigarette to a woman in PJs who had just gotten out of jail. She wanted her son back, but couldn’t get through to whomever she was trying to reach. Twice, she complimented my teeth.

We tried to go inside an end-of-times supply store, but the old man owner—friendly and mild in his yellow MAGA hat—was closing up. (Perhaps too on the nose a metaphor for, well, everything?)

We rocked up for our first night together at the Americana Motor Hotel in Flagstaff. Our room had a disco ball. Dinner was at a downtown dive: beer, Diet Pepsi, pickles, and chicken stew.

We went bowling. The alley was full of college kids doing their thing, and as we waited for a lane, we took turns ducking to the bathroom to take ketamine. High, we descended on the photo booth, and Wesley suggested a make-out. When our lane opened, I kissed him freely.

We went back to the motel and kept kissing. I excused myself to shower, and when I returned in a robe, he was lying on the bed, apparently ready to have me. We embraced and kissed again until he separated and said he was too in his head. I assured him that we didn’t have to do anything, and privately interrogated my own reasons for even wanting to.

His wavering—and his inability to articulate what was behind it—reminded me of being young and scared of sex. We changed into pajamas and coiled together tightly until we fell asleep.

Day Two: Flagstaff to Amarillo, Texas, by way of Albuquerque

The next day, Wesley and I went for a leisurely stroll, sourcing our morning coffee from the inevitable flanneled men with monosyllabic names. We admired and envied the patrons who sat in the window with their books.

At the local thrift store, I bought a $2 copper-colored pinafore dress that was surely made for a 12-year-old.

We set out late for Albuquerque. Wesley sought New Mex-Mex, and who was I to disagree? I wanted to encourage his every impulse, because he had agreed to come with me. Any route, any plate, any timeframe he needed, I would oblige.

I quickly realized that I liked giving him things, liked making him happy. I saw it as a sign of affection, affection that I was eager to let swell.

That evening, we ate ground beef nachos and honey-soapapillas. We walked around town, observed a Mass at the region’s oldest Catholic church, then strategized at Starbucks as dark fell.

We didn’t really want to drive another four hours or go through the Texas panhandle at all, but suddenly the magnitude of our trip was apparent. Wesley took the wheel for the night shift.

This is the first in a two-part series. Return to read Part II of Tootsie and Wesley’s intrepid road trip on May 20.

Tootsie Haine

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