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Internet Time Machine

My (Mutual) Breakup With Online Dating

Why I’m ending the longest relationship I’ve ever had

Illustration: Peter Phobia

This story is part of the Internet Time Machine, a collection about life online in the 2010s.

TToward 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.

ItIt 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, 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 inconspicuous—while your friends hovered at a nearby bar so you had other options.

This system had its flaws, naturally. Namely, a heavy reliance on alcohol, complete ambiguity when it came to intentions, and the need for an almost meditative commitment to going with the flow. But there was a saving grace to it all too. A beauty that, like most good things, didn’t reveal itself until it was gone.

Despite the ambiguity of the meet-up itself, you were generally meeting people you’d crossed paths with in real life. Most often at parties, events, places where there was some mutual connection between you and the other person. Of course there were exceptions. If a stranger wrote his number on a napkin in Midtown, a connection was unlikely, but—like dates themselves—that was more an image from a movie than a real possibility. Because of this, there was always some level of accountability between you and your romantic interest. In other words, if you were terrible, people would hear about it.

Accountability was the big old gift horse we all looked in the big old pre-app mouth. It wasn’t that accountability ensured that people weren’t breaking hearts willy-nilly—every generation has some version of that—but it did ensure that people at least treated one another like human beings.

It’s hard to imagine now, but when online dating first started, we mindlessly inherited this accountability practice. We treated each other like people. It didn’t occur to us not to. Rejection was delivered in the form of a bad excuse or a total lie, but not replying to someone at all—completely ignoring a person—was rare. If we didn’t click, we made something up and continued our search using a modified filter. This combination of unambiguous dates and personal accountability came close to romantic Narnia. It was all so exciting—so civil.

What none of us realized was that the accountability we afforded one another was nothing but a grandfathered-in habit, a relic from another time, completely futile when it came to the anonymity of the internet. With online dating there were typically no common friends, nothing tethering this new person to your world. They were an icon. You could make them disappear.

In 2017, the term “ghosting” was added to the Merriam-Webster dictionary. To ghost was to connect with a potential romantic interest and then completely ignore them. I can’t complain too much about it because I, too, have been guilty of the practice. It was impossible to actively date online and not be. You felt cheated if you didn’t ghost at least once in a while, like someone who lets everyone else board the subway but never gets on themselves. It only seemed fair.

By this time, apps had replaced desktop, browsing became swiping. Choosing a date no longer involved reading paragraphs about said person; now, we made an almost animalistic split-second judgment, flattening people to a single image. Instead of going to pains to compose thoughtful messages poking at a particular detail in their profile so the receiver would know we read it, we all just tossed out “heys” and hoped for the best. Between the laziness in follow-through and the fact that, chances were, one of us would likely disappear without a trace anyway, the whole charade snowballed into one big ball of apathy.

BBut I’d be remiss if I blamed it all on the apps. As online dating transformed from earnest guy who hasn’t quite realized he’s hot to a jerk who can’t get enough of himself, I, too, was changing. Or, rather, I was getting old. At 36, my profile signaled less a woman looking for a spark and more a woman ready to map out her birth plan. Matches with anyone in the vicinity of my age dropped like a step function after I turned 35, and the matches I did get seemed disturbingly eager to settle down. Never mind that my desire for a baby was still hovering somewhere around nil, I would far prefer to take my time than rush through the motions. The apps left no room for explanation.

The only thing the apps featured more prominently—for those who hadn’t filtered out women 35 and older—was my image. Unfortunately I had no idea how to take photos of myself and had no desire to learn or even try. This had never been an issue. In the old days we were all so high on the novelty of smartphones that we snapped shots of one another regularly. Unlike the millennials, well-versed in selfie-sticks and duck face (I still don’t really know what that means), my photos, once completely up to par, now seemed to convey, in the poorly-lit pixels themselves, an overt lameness.

But here’s where things really went south: As online dating grew less interested in me with every passing year, I grew more interested in me. By my midthirties, I had friends who were like family, an apartment I never wanted to leave, and work I loved. Not only had I built a life I was proud of, I actually liked myself. My interests weren’t inherited, they were earned, textured with years of self-discovery. I woke up eager to spend the day writing, had an endless supply of captivating (albeit platonic) dinner dates, and organized trips with other untethered friends. So instead of broadening my age range and entertaining “hey” messages, I got pickier; my right swipes were fewer and further between.

Reader, I got no matches. The person I’d grown proud of didn’t map to the quickly digestible criteria that had buoyed me in my youth. For the first time since I’d started online dating, I had crossed a line. I valued myself more than society valued me. I was operating at a deficit.

There are worse fates than liking yourself. Compared to my younger self, turning my life upside-down for any guy with a New Yorker subscription and a vinyl habit, my time was my own, and I loved it. When I did succumb to a date, I found myself thinking of excuses to leave, craving the company of friends, my work, even just a book. Not because men are altogether terrible—some of my best friends are men—they’re just dating 26-year-olds. Of course I’d be lying if I said I didn’t want partnership. It just has to feel equal—not on society’s terms, but on mine.

It’s been nearly a year, and I still relapse here and there. I swipe at night if I’m feeling lonely. But as is the case with most breakups, it’s for the best. At least I can remember life before online dating. That pit in your stomach when your friend’s friend pours you a drink and says that thing you’ve been thinking for years. The serendipity of it all, that somehow all the events in your life conspired so the two of you could find one another in this chaotic world, at this otherwise unbearable party, an unbelievable feat; something that, even if it doesn’t work out, is impossible to feel and then completely ignore.

Keep exploring the Internet Time Machine.

Writer and founder of Chorus, the matchmaking app where friends swipe for friends. More at (or

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