The average conventionally attractive early-30's single gal in Manhattan doesn't have to work all that hard on dating apps to find herself with a few prospects.
But I was not average. I was on a mission to date the entire city.
In 2019, before the world shut down, the dating scene was absolutely popping off in New York, and my calendar may have been popping the hardest. My first month in the city, I made it my goal to write an article detailing what it was like to go on 30 dates in 30 days, and I barely slowed down after that.
One relatively low-key weeknight I was swiping through various dating apps and happened upon a boyishly handsome actor living in the Bronx, who boasted about his self-made documentary on his profile along with a few cute photos and funny quips.
Mutually intrigued, we engaged in a bit of banter and set up a date at one of my favorite New York City hotspots, the Union Square Farmers Market.
Fresh from the salon with a bouncy blowout, on a mild early July afternoon, I made my way to 14th Street where I met my suitor among the zucchinis and tomatoes for a first date stroll. Our chemistry was instant and we flirted over remarks about our favorite seasonal produce.
Time seemed to fly by and before I knew it, we were hopping on the subway uptown to ride the gondolas to Roosevelt Island, simply because it was one of those uniquely New York things to do, that most people don't know even exists.
This charming, teasing actor seemed to have done it all in New York, the more oddball the better, and I found myself a little smitten. He gently guided me off the gondola with a friendly hand on my lower back. Despite the humidity and the fact that I was definitely sweating through my paper-thin summer dress, I was thrilled by his touch.
We shared a kiss among the fireflies buzzing around the island and once back in Manhattan, he walked me to my subway stop like a gentleman with a crush. I couldn't wait to see him again.
When he texted the following week, I was ready to say yes to anything he suggested. It was only with slight reservations that I accepted his offer for a ticket to his improv comedy show that Friday night with the promise we'd grab a bite after.
I'll admit—I watched his outdated documentary in anticipation of the date, getting ever more excited about imagining a future relationship with someone so fun and artsy. Folks, my imagination was toying with me.
Ever fashionable, I showed up to the theater about 10 minutes late, planning to sit in the back and look mysterious among fellow theatergoers, who would have no idea they were surrounding the handsome actor's real-life love interest.
I gave my name to the box office clerk who said: "Oh good, you're here. I'll tell them to start."
Into the walkie talkie she unceremoniously barked, "Tell them they can go now, Lisa made it."
Flattered, albeit slightly confused, I waltzed into the room, imagining that perhaps I had a special seat reserved for me, as the intriguing guest of the marquee star.
To my great horror, I discovered instead that the theater was empty and I represented one of two total audience members. Shoved to the front row by an anxious waiter, I was greeted by applause from the cast members who were thrilled to have doubled the audience.
That's right, the onstage performers cheered that their tardy second viewer had arrived. One even shouted: "Lisa's here!" and it wasn't even the actor I was trying to date.
They began the improv show with a skit about New York, traffic and unique annoyances that plague Manhattanites and it was all relatively fine. I laughed through the majority of the skits, mostly to trick myself into thinking I was having a decent time. As the show carried on, I came to terms with the fact that there was absolutely no way of sneaking out, the only way out of this was through it.
But the most terrible moment of this terrible date came when I was involuntarily pulled onstage for an interview, so the improv actors could design a skit about me, seemingly to entertain the—now one—audience member.
It was clever enough, with references to my affinity for farmers' markets, my ostensible writing chops and a witty little song about my California roots.
I deeply wished I wasn't being held onstage for the duration of the skit, but understood why when at the end, the actor I'd met on the internet not even two weeks prior, mock-proposed to me as the big crescendo.
I flirtily said I'd think about it and clambered back to my seat. Needless to say, the awkward energy led to an uncomfortable bite after the show. He insisted we go all the way to the Bronx for some unremarkable celebrity's favorite pizza slice.
As he ate voraciously, seemingly famished from the effort it took to ruin my evening, he recapped his entire show, as though I hadn't been a forced witness to it all. Unfazed by his choice to expose me to such an experience, he at one point declared: "I'm glad I thought to invite you to this, it's no fun when there's no audience."
Apparently, this must happen often, and I gathered that he was proud of himself for garnering an audience member, seemingly a far higher priority than securing a girlfriend. I thanked him for the pizza slice and began my hour-long subway ride home, during which I formed a policy of never attending an artist's performance as a prequel to a date ever again.
I'm embarrassed to admit that when he texted two weeks later to invite me to dinner, I accepted. With the recollection of the butterflies from our first date, I wondered if the improv events were a fluke, and if my destiny as an artist's muse awaited.
Foiled again, I was met with helpful clarity at an Italian restaurant when he spoke yet again only of himself, including a detailed rundown of the activities that worsen his terrible problem with hemorrhoids.
After we parted ways for the last time, neither to hear from the other again, I walked home through Chinatown contemplating my experience.
We would not end up together, and if he texted, I was ready to let him down gently. But I couldn't help myself from recalling the dates in detail, organizing the story in my head, and being absolutely giddy to tell my friends about it over brunch.
Lisa Holden is a dating expert and journalist who lives in San Diego, California.
All views expressed in this article are the author's own.
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