A Dating App Founder And A Dating App Novice Walk Into A Bar

My rejected Modern Love essay. At least the most recent (there have been many).

Art from Chorus, my dating app, RIP.

The moment I saw Ben, I knew he was new to dating apps. When you browse profiles long enough, you can’t help but pick up on patterns, and I was—literally—a professional. Driven by a decade of swiping that seemed to land me nothing but a handful of bad decisions, a lot of wasted time, and an uncomfortably judgmental mindset, I had recently raised venture funding and launched my own dating app.

After years of more exploratory swiping attempts, I had settled on searching for people similar to me. Specifically, men who related to my particular strain of existential dread, had also spent long stretches of time alone, and who didn’t need a relationship, per se, but longed to be understood. I was an expert at filtering my way to these matches, and though it hadn’t brought me love (or even a committed relationship longer than a few months), I was usually entangled in a “situationship” with someone who fit this bill.

When I saw Ben’s profile, I was in no place to date. It was 2020 and the world appeared to be ending, my dating app—requiring more than a minor pivot in the wake of Covid—was running out of money, and I had just moved across the country in a rash attempt to make one particularly evasive situationship work. Turns out, when nothing feels knowable, the clarity of a single goal can feel like relief, even if that goal is nothing short of self-destruction via a cross-country road trip. To no one’s surprise but my own, my attempt ended in disaster and I was left counting down the days until my return to New York. 

But that night in Los Angeles, like so many nights in 2020, I was bored and lonely, so—with only eighteen days left until my return—I went on Tinder in the name of “research,” and swiped right. 

“You’re from Brooklyn,” Ben messaged. 

This was not in my profile. 

“The backyard shot,” he wrote. “Classic Brooklyn.” Then, “I’m moving back to NY in a few months. So I want to be upfront about that.”

Moving to New York? Wanted to be upfront? “I’m also moving back to NY!” I typed too quickly.

Then I took a closer look at his profile. He lived in a house in the suburbs; I had only ever lived in city apartments. He worked with his hands; I never left my screen. His favorite book was a cookbook; I worshiped at the altar of takeout. Searching for some sign of political alignment, I found no female authors listed or Kate Bush records conspicuously placed on his shelf. 

He asked if I’d rather talk on the phone.

“Sure, what night is good for you?” I asked, so accustomed to the Tetris game of scheduling Zoom dates that I was in the process of building a feature for my app around it.

“I mean tonight,” he wrote. “I just have to put my son to bed. Can I call you in twenty?”

“Oh!” I tried to play it cool, but in truth I was dumbfounded. The openness with which he was ready to jump in. The responsibility of putting a child to bed—of having a child. The preference for a classic audio call. We were around the same age, but he felt like a lifetime older than the men I’d dated. 

“Sounds great!” I wrote, then instantly cursed myself for using an exclamation point two humiliating times in a row. It had become second nature to over-analyze messages, terrified that an extraneous punctuation or the wrong turn of phrase would leave me inexplicably un-matched. I couldn’t know it would be the last time I’d have to worry about that.

“Great. I’ll call you shortly!” 

Turns out, Ben was, in fact, brand new to the apps. Because Ben was recently—and not even officially—divorced. He was moving because his ex-wife preferred Brooklyn, where they had lived together for eleven years, and they were sharing custody of their three-year-old son. In the meantime, he and his ex were still living together in LA, though sleeping separately.

Professionally speaking, it screamed “Red Flags.” Our worlds could not have been more different, not to mention his world seemed to be falling apart. By objective standards, I should have run. But in the past decade, and especially in the past year, I’d experienced a universe of red flags, repeatedly chasing men who—despite their long-time single status—proved wholly unavailable. 

Meanwhile, this newly divorced man seemed eager and appreciative of connection. On the phone, he'd been warm and curious and nothing if not straightforward. Maybe I was crazy. Certainly I was lonely. But something in me trusted him. I was no longer bothered by the typical red. My color scheme had changed.

Our hike in Griffith Park was short so I asked if he wanted to come back to my apartment when we’d finished. He seemed surprised by my forwardness, but a decade of first dates had taught me how to spot a good one. Despite the differences in our lives there was a shared sensibility and humor that made conversation flow and laughter easy; it felt familiar—and rare. Before he left, hours later, he asked when he could see me again.  

On our third date he called me his girlfriend. “Is that okay?” he asked, misinterpreting my look of shock for disappointment.

I assured him it was. 

Then I panicked. 

“Don’t you want to date around?” I asked. I was worried for him. I was worried for me. Surely he wasn’t ready to settle down, and I couldn’t handle falling for another guy who wasn’t ready.

“Not really,” he said. “I wanted to date in order to find a great woman. And I found that.”

I’ve always been skeptical of anyone who has not spent long periods of time alone. My decade alone while often, well, lonely, was instrumental in shaping who I am. It felt impossible to relate to anyone who had moved through adulthood largely in partnership. “You don’t want me, you want a relationship,” was something I told Ben many times before I finally allowed myself to trust him when he said it was possible to want both. Before I finally allowed myself to value someone who valued relationships.

Sometimes growth comes in unexpected forms. I thought I had optimized my online dating approach—filtering for an inherent sameness in the name of connection. But it had become glaringly apparent that the men I fell for didn’t value commitment or the work required to build a life together, which left me with the devastating realization that maybe I didn’t, either. I knew (intellectually, at least) that that work was essential to the kind of intimacy I was looking for, so instead of judging this difference between us, this time, I tried to learn from it.

I delayed my flight back to New York a month to spend more time with him in LA, ashamed and terrified that I was making another decision for a man; not to mention a man who was still living with his ex-wife. He often apologized that we had to take things slow given his situation and thanked me for being so patient. But I was used to waiting days for a text message, then sifting through men’s excuses. There were no excuses with Ben, only explanations. Meanwhile, slow to him was light-speed for me; it was the fastest-moving relationship I’d had in years. 

Turns out, when you finally fall in love with a committed partner, the last thing you want to do after you’ve spent your adult life complaining about the experience of dating, then navigating the business of dating, then grappling with a pandemic that upends both the experience and the business of dating, is run a dating app. Online dating was more jumbled than ever in the wake of Covid, and I was no longer convinced that I was the best person to solve that problem, nor that an app alone was the answer. My dating app didn’t survive, but my relationship did. 

Last fall we moved in together. Even now, over two years later, it feels a little like we’re building the plane while flying it. Ben still needs time and space to process his divorce, which, as someone who cherishes time alone and adores self-reflection, I’m more than happy to give. It’s a bump to navigate, but I was so used to navigating mountains in my dating life, this particular hill feels immensely doable. 

We often joke that I was the expert during our early days of courtship—knowing from the start that this had potential, navigating his nerves, making the first move—and he the expert at commitment—reminding me that we don’t have to break up whenever we get into a fight, making plans more than a week in advance, and sharing his feelings about us and our future in a way that, for a long time, felt like another language.

Sometimes, I still worry that Ben and I are too different, that he doesn’t get me like the angsty, loner men I once obsessed over. Ben has not been maneuvering on the apps for years learning the talking points of progressive women, he doesn’t understand—in his bones—my fury towards modern dating and its inherent inequities, and, as an eternal optimist, he will not nod in agreement when I detail my incessant existential dread.

But then he listens as I go on about my day, not sharing my sensibility exactly but stashing it away so he can remind me of myself later on when I need it. He’s eager to spend time with my family and friends, even when my body freezes up asking, so used to a man going cold at the hint of a need. He enjoys cooking for hours, and I enjoy his meals being delivered to me on the couch. 

And then I ask myself what it means to get someone, to be understood. Maybe it’s not being the perfect “match” as online dating wires us to assume. Maybe, there’s no filter for what really matters—someone who listens and cares and is ready to put in the work to make something last. We just need to wait, sometimes for a very long time, and hope we’re ready to do the same when we find it.