Hacking the online dating system

I was 22 by the time I realized I was lonely. By any other measure I considered myself successful: I’d gotten through high school, college, and my first year at a steady professional job that was better than the jobs my parents had. I biked to work, cooked all my own meals, and rented a studio apartment in a fancy clean city. But I’d never, ever, been on a single date, and now this thought that had never seemed to matter much before had become a constant and intrusive source of misery.

I had no idea where to begin trying to solve this problem. By this point I’d personally heard about half the people in my friend-network repeatedly use words like “virgin” in a disparaging tone, so I didn’t feel safe opening up to them. The couple of friends I did trust enough to talk to were sympathetic but had no advice and could offer no help (they and pretty much everyone they knew were already partnered up and/or already knew they were not interested in me). So I started searching through books and internet advice columns.

By this point (2012), the most visible dating-related internet resources already seemed pretty polarized. A substantial amount of it came with some pretty terrible dehumanizing rhetoric, so I ignored it; if the alternative was absorbing a blatantly toxic worldview, I figured it was better to just keep being miserable. But a lot of the non-terrible places were having to spend lots of time and effort trying to counter the terrible ones. Many Doctor Nerdlove blog posts explained how important it was to treat women just like people, and make friends with them, and be authentic. Others explained how to handle a bad date, or in some other way progress further with an existing interested person. Relatively few described any kind of explicit model for what was supposed to happen in order for dating to begin, to be possible, and those seemed fairly patronizing: wear clothes that fit, practice daily hygiene, that sort of thing.

I eventually concluded that maybe I just couldn’t learn anything further from reading without first going on a couple of dates to get more context. Of course, the root problem seemed to be that I didn’t know what arranging a date would look like in the first place, but from all available evidence it didn’t seem like anyone suspected my guesses would be any worse than theirs.

At 23, I’d had many engaging (if brief) conversations with strangers on the train, introductions to new friends-of-friends-of-friends, and casual hellos with passers-by near bookstores, libraries, and casual restaurants. I had even asked some of those people if they’d like to meet again for coffee, dinner, or similar. All politely declined. I was an active nightly user of both OKCupid and Tinder. I gave OKCupid some money. I posted candid photos, answered questions, wrote short essays, and sent messages. One woman I hadn’t sent a message to sent me a message. We lived on opposite sides of our state. We became penpals.

I did some more research, this time including a couple of slightly more questionable sources. It’s a numbers game, they argued. There’s little to no harm in asking, so just ask lots of people. Hang out at places where lots of people go to hook up. Get used to being rejected a lot; it’ll make you more comfortable.

I thought I was already pretty familiar with rejection by this point, but I did what they said. I asked over one hundred women. All but two politely declined; those other two ghosted me instead. I hung out at bars and hated it. I walked around town and wished I was back at home. I sat at home and cried, a lot.

When this whole thing started, I’d felt lonely. I was sad that I hadn’t yet found that kind of connection with anyone, and that I hadn’t gathered any evidence yet for what I might or might not want beyond that. I’d regretted that I hadn’t started earlier. After almost two consecutive years of deliberate effort and no observable progress, I was in despair. By the numbers, if you put all the people I’d talked to in a room, you could find at least one person who’d disagree with the others on vaccinations, the moon landing, or where the President was born. There was just one thing they’d all agree on: I wasn’t worth one single hour of their time.

My 24th birthday came and went. My new job was too far to bike, and public transit technically reached but left little time for any offline hobbies. I started participating much more heavily in chat rooms, forums, and blog comments sections, generally along the theme of dating trouble or dating advice. I eventually saved up for driving lessons, a license, and a car, but I kept complaining on the forums.

A couple of people suggested I might be asexual, which turned out to be really helpful. I didn’t know other people were or could be like that, and the label conferred a sort of vague sense of belonging to a community, even if I’d never have many interactions with them or have much of a reason to “come out” about it to anyone else. It was also a theory that very elegantly explained why at least some of the women I’d had lengthy, positive interactions with didn’t see me as a person they’d want to date: there was literally no chemistry between us.

Unfortunately, this still didn’t do much to suggest a solution. Even in a big city, there aren’t that many asexual people looking for romantic partners. I kept looking anyway, but it never really led anywhere.

I turned 25. By this point I’d tuned my OKCupid profile dozens of times. I’d read a few series and watched a few TV shows that seemed to interest most of the people OKCupid claimed were my matches, and added the ones I liked. I’d done my best to follow the practices described by Amy Webb and Chris McKinlay, but I felt a little dishonest about manipulating people to look at my profile so I made a spreadsheet explaining how it worked and included it on the profile. I shotgunned a bunch more messages to a random subset of the new people OKCupid found.


One day, I just got really frustrated. Nothing was working, not even these contrived solutions tailored to socially-awkward mathematicians and engineers. I vandalized my own spreadsheet with angry criticisms of the ways OKCupid phrased their questions, the interface design choices, and of course the broader culture around dating that leaves clumsy tools like this as the best available option for a lonely adult.

Seemingly by sheer luck, one of the next people who viewed my profile was a woman with strong opinions about social engineering and careful framing of survey questions. She sent me the first message, and now, four years later, we are married. I couldn’t have imagined a better partner.

I’m sorry to observe that my story offers little in the way of actionable advice, other than (perhaps) the suggestion that more people might try to “hack” online dating (but like Amy Webb, not like Stanley Jobson), or that OKCupid fix its $#!^ already so the rest of us don’t have to. The more abstract point I hope to convey is: finding love can be really difficult and take a really long time, but it can also still be absolutely worth it. I hope that helps.

Nearly Takuan

"nearly" works in the software industry and lives in Portland, Oregon.

This Post Has 3 Comments

  1. Very well done. Shows that sheer persistence can get results. Perhaps also that being different attracts attention, some of it positive – and that’s all you need.

  2. Do you think your rejections had to do with a physical trait, for example height? I know I get rejected a lot for being short. How tall are you?

  3. “The more abstract point I hope to convey is: finding love can be really difficult and take a really long time, but it can also still be absolutely worth it. I hope that helps”

    Worth it? Of course you’d feel that way; it’s the kind of admission one makes only after having ‘made it’.

    I’m not angry that you found what you were looking for, I’m really not. There’s just a part of me that wishes I was happy for you.

    Take care.

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