Seeking Flings—Then Giving Them Up

I knew I had Jack that first night...Boys like me, although that doesn’t mean they stick around, so I was now choosing men who wouldn’t.

The Way We Were (1973)

The Way We Were (1973)


I was scouring the Mandalay Bay Convention Center on a quest for a Vegas fling. At nearly 36, I was in the throes of a lengthy, first-time boy binge after several outlook-shifting heartbreaks, including a brief, doomed marriage and another excruciating broken engagement. I now feared male dismissiveness and my own judgment, but I paraded my distress as indifference. I sought temporary diversions, convincing myself I didn’t require commitment for sustained happiness; it wasn’t true.

Underneath a semi-hardened exterior existed a still-sensitive girl who’d always wanted her own family. I no longer believed I was worthy of one, however. Multiple lost loves had beaten down my once fragile sensibilities.

At this trade show, I spotted an attractive young man in a booth down one of the aisles. I’d met him before at a one-day trade show in Illinois that didn’t lend itself to overnight dalliances like Vegas. Here was my chance.

He was tall and slim, with green eyes and black hair, despite his Irish last name.

I approached him. He remembered me. I was in.

We exchanged business cards. Jack. Sales Associate. Connecticut.

"What are you doing later?" he asked, after a few minutes of chit chat.

"I have to go to a PR dinner," I said.

"I have to go to that too!" he said. "I didn’t want to go, but now I kind of want to."

Jackpot! Who needs slot machines and blackjack?   

"We don’t gamble with money; we gamble with our lives," a friend said later.

At dinner, Jack, his female coworker, and their boss were situated at a table in the corner. I slid in next to twenty-eight-year-old Jack and didn’t budge. I became more attracted to him the longer we conversed. We talked about our hometowns, our past relationships, and our siblings, while the four-star restaurant served up fancy cabernet and gourmet treats.

By the end of dinner, I’d slid my hand along Jack’s black dress slacks under the white table cloth, squeezing his slender thigh as I leaned in toward him during a flirtatious moment. Sparks flew with our faces inches apart, our breath shallow and quick. He was drawn to me as much as I was to him.

"What are you planning to do now?" Jack asked after dinner.

"Whatever you’re doing," I said.

"That’s what I thought."

I sprinted to my room for a rapid freshen-up. I brushed my teeth and hair, spritzed perfume across my neck, and applied another layer of deodorant. I was becoming an expert prepper, and I was about to have sex with a delightful east coast stranger. I was exuberant.

I headed downstairs, where Jack was talking to his female coworker at the bar. He then balanced the intriguing fine line between aloof and attentive with me. When I left to use the restroom, Jack said, "I’ll go with you."

In the middle of the casino, we kissed. The gambling noise faded. For an instant, we were the silent apex of the bustling city.

"Whoa," we both said, looking into each other’s eyes as we eased our soft lips apart.

Our physical connection was undeniable, but it was difficult to lob clues at Jack that I wanted to take him to my room. Back at the bar, as he talked shop with a male colleague, I ran my hand under Jack’s buttoned-down white pinstriped shirt, up his back. I slipped my fingers under the waistline of his dress pants, and slid my hand across his lower back and around his lower belly. I got chills. He didn’t flinch.

Why are they still talking about work? I thought.

"I don’t even know why we’re still sitting here," I finally said.

Jack set down his cocktail.

"Right, we’re gonna take off," he said.

Hotel room sex with Jack was spectacular, especially for a first time: an open, playful dialogue, oral sex, mutual orgasms, and a shared shower.

"That was a good session," he said, satisfied as I walked him to the door. I’d never heard anyone call sex a "session" before. I found it humorous, as if I were a hired masseuse.

I dozed off at 2:00 AM with visions of a repeat performance the next night. I was pleased I’d scored the first night; that gave us time for more, I thought. I wasn’t content with a one-night stand, but I’d gradually lowered my expectations. I didn’t want a long-distance boyfriend. I didn’t plan to talk to Jack after Vegas, but I geared up for a two-night stand, and I thought I had it wired. My expectations were still slightly above zero.

Day two: I sent Jack a text at 6:00 PM. He was gambling at the MGM Grand. He said he’d get back to me. Silence followed. At 10:00 PM, I put on pajamas, cried, and settled in for a night of TV and disappointment. I awoke in the morning to a 2:00 AM text.

"Hey, come out and meet us!" it read.

Really, dude?

"I’m checking out of my hotel today," I wrote back.

"I thought we had another night!" he responded.

"Nope, I’m leaving."

He sent a sad emoji face.

After the trade show closed, I met Jack and his boss at the pool before I left for the airport. The warm, fresh air was welcome after an exhausting few days indoors.

Jack was out of his classy work clothes, shirtless, sporting a blue bathing suit and a thick, sleazy gold chain around his neck nestled into his dark chest hair. It was an unforeseen and instant turnoff. In the harsh sunlight, he blended in with the other douchebags flanking the pool.

Yet, as he sunbathed, I sat in the lounge chair next to him, leaned over, and ran my fingers through his soft chest hair.

I can always strip him off that dumb necklace, I thought.

He didn’t balk, but he was no longer receptive. Our affection now felt one-sided. He placed his hands behind his head and leaned back to sunbathe as if to say, "Worship me."

Soon, I walked him to the casino, where we had a quick peck goodbye, a stark contrast to our seductive first kiss in the same spot only two nights before.

It’s been real. Have a nice life, I thought.

I returned to the pool, where Jack’s boss handed me their room key.

"Go surprise him while he’s taking a shower," he said.

I was hesitant, not in the mood for the rejection I’d prearranged.

I gripped the rectangular plastic room key, pondering a surprise quickie. It was tempting.

I sent Jack a text.

"Your boss gave me your room key and told me to surprise you."

"That’s funny, but I’m shopping right now."


"Shopping?" his boss asked, incredulous, shaking his head.

I later found Jack in the hotel lobby two-fisting plastic bags stuffed with new designer clothes.

I flashed him the in-person version of the sad emoji face.

"I know, right?" he smiled and walked away.

I never talked to him again.

In my mid-30s, my initial confidence level with attractive men didn’t match my perception of enduring relationship success; I felt doomed to fail on a protracted timeline. In this instance, and others, I chose to pursue someone based on the short-term nature of the possibilities. I knew I had Jack that first night. Boys like me, although that doesn’t mean they stick around, so I was now choosing men who wouldn’t.

Despite the second night’s letdown and the ill-timed shopping trip, I have fond memories of that first night. As a still-single woman in her early 40s, however, I’ve long since stopped pursuing temporary attention. I grew wiser with regard to my own big picture needs, and my priorities changed. While incidents like this one were satisfying, they were so only in the way eating a chocolate sundae is fulfilling: After scraping the bowl clean, I’d feel a tad ill and wish I’d had the forethought to resist shoveling in the first spoonful.

Although arbitrary, loveless sex doesn’t add two pounds to the gut like that sundae would, the delicious indulgence is fleeting. Anecdotes don’t nourish real happiness for me. While there’s nothing wrong with two consenting people having a brief rendezvous, I personally am not cut out for casual sex. I want a long-term relationship, and I now hold out hope for genuine love like I once did as a virtuous teenager. I no longer have the energy for guys swathed in ostentatious jewelry who’d rather shop than see me naked. As a friend recently said, “Love is your birthright.” It’s a simple, yet profound, concept I’m starting to believe again.

Chelsey Drysdale is a writer and editor on a road trip in the Pacific Northwest. Her essays have appeared in Book Lovers: Sexy Stories from Under the Covers, Black Fox Literary Magazine, Brevity, Reservoir Journal, and Bustle. She is a contributor in The Best Advice in Six Words and CRUSH: Writers Reflect on Love, Longing and the Lasting Power of Their First Celebrity Crush. She is a current Pushcart Prize nominee and is seeking representation for her completed essay collection, Yes Girl.