How a Math Genius Hacked OkCupid to Find True Love

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.

McKinlay, a lanky 35-year-old with tousled hair, was one of about 40 million Americans looking for romance through websites like Match, J-Date, and e-Harmony, and he’d been searching in vain since his last breakup nine months earlier. He’d sent dozens of cutesy introductory messages to women touted as potential matches by OkCupid’s algorithms. Most were ignored; he’d gone on a total of six first dates.

OkCupid was founded by Harvard math majors in 2004, and it first caught daters’ attention because of its computational approach to matchmaking. Members answer droves of multiple-choice survey questions on everything from politics, religion, and family to love, sex, and smartphones.

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 hookup Mobile, 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.

But mathematically, McKinlay’s compatibility with women in Los Angeles was abysmal. OkCupid’s algorithms use only the questions that both potential matches decide to answer, and the match questions McKinlay had chosen-more or less at random-had proven unpopular. When he scrolled through his matches, fewer than 100 women would appear above the 90 percent compatibility mark. And that was in a city containing some 2 million women (approximately 80,000 of them on OkCupid). On a site where compatibility equals visibility, he was practically a ghost.

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.

Instead, he realized, he should be dating like a mathematician

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

On that early morning in , 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

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.

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