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FRIENDS & BENEFITS

My First Date on a $119 Celebrity Dating App Was a Letdown

I waited a year to join. My first match was disappointing.

Fireman holding woman

Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty


Welcome to Friends and Benefits. Follow Tootsie Haine, 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.

After a year of waiting, I got accepted to Raya, the supposedly exclusive dating app whose male members, I had been told, were mostly perplexingly gorgeous models as well as the occasional micro and/or withering celebrity.

I was drunk when I got the acceptance text, and so I immediately spent $119 on a yearlong membership. My first date from the app was Kurt, a freelance TV writer. We met at an old firehouse-turned-cocktail bar with dark academia-style interiors. When I arrived, he was already slurping a Hot Toddy.

Kurt was tall, slim, and as vague as a shadow. Blink, and you’d miss him. He told me to get anything on his tab. I had three Diet Cokes and a barman’s jar of mixed olives. We talked about The White Lotus and discovered we drove the same make of late-2000s car.

He told me he loved it so much he’d got a tattoo of his car key. I insisted he unbutton his sleeve to show me and, upon seeing it, said something like, “Oh… Wow.”

A sailor aboard the U.S.S. New Jersey inspects another sailor's tattoos in December 1944.

Kurt told me he got a tattoo of his favorite car. I insisted he show it to me, then went on a tirade about my disdain for tattoos, remarking that they exude conformity.

Historical/Corbis via Getty Images

I then went on a tirade against tattoos, telling him I found them to typically be a symbol of conformity, but admitted that several of my friends seemed much happier after covering themselves in them.

I insisted he unbutton his sleeve to show me his tattoo and, upon seeing it, said something like, “Oh… Wow.” I then went on a tirade against tattoos—I thought they symbolized conformity.

Exactly one and a half hours after the date began, Kurt announced that he was tired—it was just before 9 p.m. on a Thursday—and was going to grab the check.

One and a half hours is how long many basic social media love gurus tell women to stay on a first date (and no longer) to leave the man wanting more, remain a creature of mystery, and, sure, maybe also get on with your life.

Cocktail glasses and couple about to kiss.

I left the firehouse feeling, well, burned. Besides the fact that I wasn’t sure if I was sexually attracted to Kurt, I had thought before its abrupt ending that the date had gone well. He was very funny.

Dennis Hallinan

I assumed that Kurt was employing no such tactic, rather that he just hated me. When I looked from our table to the bar, I couldn’t see him, and quickly convinced myself he had walked right out.

I was surprised when he returned to the table a couple of minutes later and asked me about my job. Too in my head to answer, I told him I feared he’d ditched me because he thought I was mean. He said that wasn’t the case; naturally, this meant I then imagined he saw me as a deeply insecure a-----e.

I offered to walk him to his car if he waited while I used the bathroom, unless he just wanted to say our goodbyes then and there.

“Yeah, let’s do that. Goodbye.”

“It was nice meeting you.”

I left the firehouse feeling, well, burned. Besides the fact that I wasn’t sure if I was sexually attracted to Kurt, I had thought before its abrupt ending that the date had gone well. He was very funny. How many people really make you chuckle? Few. He was educated. He had the job I wanted. He was cordial.

1983: British actress and former model Rachel Ward and Richard Chamberlain in the television drama "The Thorn Birds."

I hadn’t been lonely, but the rejection stung, and though I didn’t really want him, I was suddenly ashamed and no longer satisfied with my own company.

Hulton Archive/Getty Images

On the one hand, I was impressed with Kurt for calling it quits. I had difficulty inching away from any dalliance, any date, good or bad. On the other, though, his disinterest was haunting.

I hadn’t been lonely, but the rejection stung, and though I didn’t really want him, I was suddenly ashamed and no longer satisfied with my own company.

In my car I did something I had been lightly putting off for weeks: I left a voice note for a guy I had seen once or twice but hadn’t bothered to date in any real way. (Yes, that would be Dylan, the best sex of my life.)

“Bad dates” don’t necessarily have a culprit or catalyst—the initial intentions of the involved parties are often innocent, even optimistic, which can make them all the more damaging. Until your self-respect is strong and you have a clear idea of what you want, it may be best to stay home.

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.

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