A Dating App Founder and A Dating App Novice Walk Into A Bar
Finding love in unexpected places after a decade on the apps.
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…
