How a Math Genius Hacked OkCupid to Find True Love
Mathematician Chris McKinlay hacked OKCupid to find the girl of his dreams. Emily Shur
Chris McKinlay was folded into a cramped fifth-floor cubicle in UCLA’s math sciences building, lit by a single bulb and the glow from his monitor. It was 3 in the morning, the optimal time to squeeze cycles out of the supercomputer in Colorado that he was using for his PhD dissertation. (The subject: large-scale data processing and parallel numerical methods.) While the computer chugged, he clicked open a second window to check his OkCupid inbox.
On that early morning in June 2012, his compiler crunching out machine code in one window, his forlorn dating profile sitting idle in the other, it dawned on him that he was doing it wrong. He’d been approaching online matchmaking like any other user. Instead, he realized, he should be dating like a mathematician.
On average, respondents select 350 questions from a pool of thousands—“Which of the following is most likely to draw you to a movie?” or “How important is religion/God in your life?” For each, the user records an answer, specifies which responses they’d find acceptable in a mate, and rates how important the question is to them on a five-point scale from “irrelevant” to “mandatory.” OkCupid’s matching engine uses that data to calculate a couple’s compatibility. The closer to 100 percent—mathematical soul mate—the better.
He realized he’d have to boost that number. If, through statistical sampling, McKinlay could ascertain which questions mattered to the kind of women he liked, he could construct a new profile that honestly answered those questions and ignored the rest. He could match every woman in LA who might be right for him, and none that weren’t.

Chris McKinlay used Python scripts to riffle through hundreds of OkCupid survey questions. He then sorted female daters into seven clusters, like “Diverse” and “Mindful,” each with distinct characteristics. Maurico Alejo
Even for a mathematician, McKinlay is unusual. Raised in a Boston suburb, he graduated from Middlebury College in 2001 with a degree in Chinese. In August of that year he took a part-time job in New York translating Chinese into English for a company on the 91st floor of the north tower of the World Trade Center. The towers fell five weeks later. (McKinlay wasn’t due at the office until 2 o’clock that day. He was asleep when the first plane hit the north tower at 8:46 am.) “After that I asked myself what I really wanted to be doing,” he says. A friend at Columbia recruited him into an offshoot of MIT’s famed professional blackjack team, and he spent the next few years bouncing between New York and Las Vegas, counting cards and earning up to $60,000 a year.
The experience kindled his interest in applied math, ultimately inspiring him to earn a master’s and then a PhD in the field. “They were capable of using mathematics in lots of different situations,” he says. “They could see some new game—like Three Card Pai Gow Poker—then go home, write some code, and come up with a strategy to beat it.”
To find the survey answers, he had to do a bit of extra sleuthing. OkCupid lets users see the responses of others, but only to questions they’ve answered themselves. McKinlay set up his bots to simply answer each question randomly—he wasn’t using the dummy profiles to attract any of the women, so the answers didn’t matter—then scooped the women’s answers into a database.
He would have to train them to act human.