How A Math Genius Hacked OkCupid To Find True Love

Who doesn’t like a good love story? Well, some people don’t I suppose, but for the majority of us love stories make us feel good and give us hope about what could be out there for ourselves. Not all love stories are the same though. They’re not all full of roses and candy and whimsical romantic dates. How about a love story that’s full of formulas, algorithms, codes, and data? This may be one of the most unromantic love stories we’ve ever heard. Who needs poems full of romantic words when you have computers full of mathematical equations?

This is Chris McKinlay. He was a 35-year-old mathematician who was living in Los Angeles and looking for love like so many other people in the world. He was part of a large group of Americans, 40 million Americans to be more specific, who were trying to find love or some sort of relationship on dating websites. McKinlay could be known for many different accomplishments, but the one thing that he will certainly be remembered for is what he did to find love on his dating website of choice, OkCupid.

A Little History

McKinlay is now a mathematician, but he didn’t start out on that journey. He grew up in a suburb of Boston and in 2001, he graduated from Middlebury College, a private school in Middlebury, Vermont. He earned a degree in Chinese, a far cry from being the math expert he would eventually turn out to be. While there is plenty of work out there for an American with Chinese language skills, that was not what would end up being the degree and skill set that would turn McKinlay into the infamous dating website hacker and data scientist that he is today.

First Job Out of College

As we mentioned, McKinlay graduated from Middlebury College in 2001. He then landed a part-time job in August translating Chinese into English for a company. His office was located on the 91st floor in the north tower of the World Trade Center. Five weeks after he was hired, the attack on the towers took place. McKinlay was not at work at the time of the attack. He was sleeping at home. He was scheduled for work that day at 2 p.m. The north tower where he worked was hit by the plane at 8:46 a.m. His work timeline that day saved him, but the attack opened his eyes that he wasn’t doing what he wanted to be doing. It was time for a change.

What Came Next

It’s funny how narrowly escaping death can make you think deeply about your life and almost gives you permission to make decisions that will alter your path in a major way. But it does do that for many people. McKinlay decided that he wasn’t doing what he wanted to do. He had a friend at Columbia University that pulled him into a group of blackjack players. The group was basically a spin-off of the MIT blackjack team that would eventually be featured in a Hollywood film about their story. McKinlay started traveling between New York and Las Vegas, counting cards and making about $60,000 per year.

His Passion Emerges

McKinlay spent a couple of years making his Vegas runs. During that time, he got to see the team he was working with using mathematics to beat the games that were played in all of the casinos. He was fascinated by it all. He said they would choose a different game and then spend a little time writing up code that gave them a way to beat it. They did that for several different Vegas games. The exposure he got to what mathematics could be used for is what inspired him to want to pursue degrees in the field of applied math. He would eventually earn a master’s and a PhD in that subject.

Flash Forward

So fast forward through the pursuance of his master’s degree, and then we find McKinlay in his cubicle on the fifth floor of the math sciences building of the UCLA campus where he worked. He is working on his dissertation for his PhD in the wee hours of the morning. He’s in the thick of processing large-scale data and parallel numerical methods through the use of a supercomputer located in Colorado. His mind wanders to a different topic, his love life, or lack thereof. He opens up the inbox for his OkCupid account. The number of messages waiting for him? Zero.


OkCupid is a free dating site that was founded by a group of Harvard math majors in 2004. The website uses algorithms to find matches for its members based on a number of different things. People were drawn into this particular site because it was using an approach that was based in mathematical computation. There are thousands of questions that each member can select from to answer. An average of 350 questions are chosen by each respondent. They are multiple choice. The member chooses his or her answer and then rates the question in terms of importance using a 5-point scale. Members are then given a percentage match rate indicating compatibility with others on the site.

Doing It All Wrong

It was June of 2012, and McKinlay had been single for the last nine months. After opening his empty OkCupid inbox, he sat thinking about his quest to find love and why he was so unsuccessful. He had been sending messages to different women on a regular basis, but he rarely would get any kind of a response. For all of his efforts, McKinlay had gone on a measly six first dates facilitated by his OkCupid profile. So, what was the problem? Where was he going wrong? It dawned on him that night. He was approaching dating online too idly. He was a mathematician. He needed to date like one.

Getting to Work

At this point, McKinlay knew what he was doing wrong, but he had to figure out how to fix it. He started thinking about how OkCupid’s matching process worked. The algorithms used in the match calculations were based on questions that both people in a possible match had answered. That meant that he had to be choosing to answer questions that others were choosing to answer as well. That alone should increase the amount of the matches he would see because he figured out that the questions he chose to answer were not the most popular.

The Questions That Matter Most

The next step for McKinlay was to find the questions that he needed to answer in order to increase his matches. So, he wanted to figure out what questions mattered the most to the type of woman he was looking for. His plan was to answer the questions honestly, but he just needed to know what the questions were. He cast his dissertation aside and started using Python scripts to run through the survey questions on the site. Then that would allow him to categorize women into different groups.

Fake Profiles

McKinlay created 12 fake OkCupid profiles to run on Python scripts to help him with his investigation work. Through the profiles, he was able to gather information about women using the dating app. He was collecting details about them and what their survey question answers were. To get the survey answers, he had to have the answers completed on all the profiles he had created. He just wrote that into the script he had been running on the profiles, then he put all of the gathered information into a database.


As you would expect, OkCupid does have security systems put in place to keep people from doing the exact sort of thing that McKinlay was doing. The system can tell if something is behaving like a computer or a human. He started seeing his profile bots getting banned one at a time. McKinlay reached out to a friend who helped him to add features to his scripts that would cause the bots’ actions to look more human. He had to bring in another computer to run 24 hours a day so that the security system wouldn’t pick up on what he was doing anymore.

His Cubicle, His Home

The data had been collected, on to analyzing it. McKinlay had the answers to 6 million questions from 20,000 women that were all around the country. He ended up letting go of his apartment and just moving into his cubicle at work. He slept there most of the time anyway. He turned his attention to figuring out the patterns that he could find in the data he had collected. He set to work using an algorithm called K-Modes to separate the women into groups based on categorized data that could be clumped together.

McKinlay’s Seven Categories

The seven groups were: “God,” “Diverse,” “Mindful,” “Tattoo,” “Dog,” “Samantha,” and “Green.” After his initial statistical sampling, McKinlay wanted to test what he’d found to that point. So, he gathered new samples from San Francisco and Los Angeles from women who had joined the website recently. He ran them through the algorithm and the results showed that this sample of women grouped the same way as the original. His system was working so far. His biggest task now was to decide which of the categories would be the best matched for his tastes.

The Women He Liked

Weeding through the clumps of women, McKinlay found that some of the groups were too much of one thing or another. But he found there was one group that drew him in. The group was full of women who were artists or musicians. These were the creative indie types who were mostly in their mid-twenties. One other group he decided he liked was one with women who were a little bit older and who were also creative but had professional jobs like designing or editing. He chose to attempt to find love somewhere within these two groups and set up two profiles, one that would be best for the first group, and one that would be best for the second group.

Optimizing for Success

McKinlay decided on 500 questions to answer for his profiles based on what he had found in his research. The questions were the most popular ones for the two groups he had chosen. He answered all of them as himself because he wanted the relationship he found to be started with honesty, not some computer-generated version of himself. He did elicit the help of the computer to figure out how much weight to assign to each question though. He used another algorithm for that called adaptive boosting.

The Dating Begins

McKinlay finally was getting noticed and matched with women that fit the descriptions of what he was interested in. He started going on dates. None of his early dates were that good. He even had one at a bar in Koreatown. That one ended with him so drunk he didn’t even remember a lot of it when he woke up in his cubicle hungover. McKinlay had so many matches to choose from that he started going on very casual dates and even doing multiple dates in one day. By the end of the summer, he had been on 55 first dates without much success.

In Steps Christine

Finally, McKinlay received a message from Christine Tien Wang. She was 28 years old and the app showed that she was a 91 percent match for him. She was an artist and when her search had resulted in bringing up McKinlay’s profile, she happily sent him a message. The two quickly planned to meet up. It was his 88th first date since starting this project to find love. McKinlay could feel the connection instantly and on that first date, he confessed the whole story to Christine. So, what did she think about the crazy, twisted story?

Together Forever

“I thought it was dark and cynical, I liked it,” says Christine of the story McKinlay shared with her. The two went on several dates over the next two weeks and then they both took down their OkCupid profiles. They connected instantly on the deep level McKinlay had been looking for and one year later they went back to the sushi bar where they had had their first date. During an interview with the two, Christine was shown the notebook where McKinlay had kept all of his notes on the women he had dated and all of what he was learning along the way. Christine gets a kick out of some of what she reads, including a note about taking two different women to the same beach on the same day. She says, “That’s horrible,” with a little laugh.

The Fairytale Ending to An Un-Fairytale

Christine ended up taking a job that put her in Qatar for a year. The two stayed in contact over Skype on a daily basis. She would also make trips home to see McKinlay from time to time. On one particular Skype call just a week after one of her visits home, Christine got the surprise of a lifetime. McKinlay pulled out a diamond ring on that call and put it up in front of the camera for her to see. Without any calculation involved, McKinlay asked Christine to marry him and she said yes! The pair are now a happily married couple after finding love on OkCupid, even if the approach was just a little unconventional.