This story is part of the Internet Time Machine, a collection about life online in the 2010s.
Toward the end, I only did it at night. Penciled it in like a chore I could perform while half asleep, watching whatever new cable drama happened to be capping my days. I could tell with a glance: not so much whether a relationship with the person on my screen could work, but whether it’d even be worth a shot. And 60 minutes later, tired and ready for bed, I’d have no more romantic prospects than when I started. But at least I’d felt like I tried.
It wasn’t always that bad. In the beginning, online dating was like my teenage dream come true: knowing when someone I liked, liked me back. I’d have a date lined up nearly every night, sometimes two in a day, my stomach full of butterflies and happy hour specials. Some dates even turned into relationships, at least for a few months at a time.
But none outlived my relationship with online dating itself, which spanned almost eight years. Looking back, our split was inevitable. Like most breakups, it’s no one’s fault and everyone’s fault. It changed, I changed, the world changed.
It was 2011 when I signed up for OkCupid, and I only did it for a guy I’d met at a party. This was back when the word “tinder” referred to flammables, Match was known as Match.com, and I was under the impression that online dating was reserved for the socially inept. But after Party Guy admitted to voluntarily taking women on legitimate dinner-and-a-movie dates—and after nothing but a quick internet browse—I signed up that night.
My generation—hovering awkwardly between Gen Xers and millennials, relating to both and fitting in with neither—exists in the intersection between earnestly dating without technology and completely and utterly relying on it. When I became of dating age, what “dating” even entailed was an abstract concept I’d absorbed from old movies. My generation did not date. We “met up.” Meet-ups involved texting your romantic interest around midnight on your flip phone to coordinate a meeting spot close enough to one of your apartments—both convenient but…