The Modern Cupid’s Arrow


The Modern Cupid’s Arrow

The Indy sits down for a conversation with Datamatch’s Supreme Cupids 




Each February, as classes start to heighten in intensity and the most dreaded of Hallmark holidays rears its head, Datamatch returns to provide a welcome reprieve. This enigmatic dating website has long been shrouded in mystery. With a survey of twenty witty questions, a mysterious proprietary matching algorithm, and the seductive promise of food for those brave souls willing to venture forth and attempt to make a new connection, Datamatch is one of the highlights of an otherwise rather grim February. Over the past several years, the annual survey has expanded from a relatively small and obscure Harvard tradition to a massive event now spanning twenty-six different universities and is only growing bigger each year. We sat down with Supreme Cupids Ryan Lee ‘20 and Theodore Liu ‘20 to find out more.

Much of Datamatch’s history is shrouded in mystery. It began in 1994 as a paper survey that was handed out to students. The Supreme Cupids of the time would stay up all night, trying to determine which lovelorn students had the best chance of finding a spark. This continued without incident until 1997, when catastrophe struck. The details of what transpired that day seem to be lost to the ages, but rumor has it that a bottle of champagne and no small amount of fire was involved. As with all matters of the heart, things drastically improved with the incorporation of the dynamic matching algorithms because nothing says love quite like thousands of lines of proprietary code. This brings us to a few years ago. The questions were ready, the mysterious system we all know and love was fully implemented, and Datamatch was ready to help people find their valentines. Enrollment, however, remained low. In an effort to increase engagement, the Supreme Cupid at the time decided to use club funding to sponsor free dates for matched users, and in doing so added the secret ingredient that turned Datamatch into the match–making juggernaut that it is today.

To quote Supreme Cupid Lee “Datamatch is about giving people an excuse to make new bonds and connections, and maybe there will be a spark.” The promise of free food gives people an excuse to sign up and a reason to follow through with their matches. The claim that people are “just doing it for the waffles” makes it easy to put themselves out there and try to make a new human connection without the usual awkwardness of such endeavors. Some people get lucky and the prophetic powers of the Datamatch algorithm guide them to something special. Many couples have started this way as well as, if rumors are to be believed, a handful of engagements. Worst-case scenario, it’s just a bad date and there is still free food. Most of the time, romantic optimism and Harvard go together like oil and water, but Datamatch encourages everyone to take a break from the all-consuming grind and give a new person a shot. From one perspective, Datamatch is just a particularly quirky college dating site, but at its core is its purpose to help students find the relationships that make the long grey winters seem just a little less bleak.

One beneficiary of the romantic powers of Datamatch shared his particularly sweet story with us. In October 2018, he decided he was going to find a meaningful romantic relationship. To self-motivate, he made a reservation four months out for a romantic dinner for two on Valentine’s Day. Cut to February 13, and he was still very much single. Going into the final few hours before Datamatch went live, he told one of his friends about his plan. She, as any good friend would, mocked him for his optimism. Datamatch went live the next morning, and he searched for his friend and hit match. A few minutes later, he received an email saying she had matched him back. He reached out saying they should hang out, and she responded, “Why don’t you take me to that dinner reservation?” They have been going steady ever since.

The team behind Datamatch is committed to helping people make these connections, and many students work incredibly hard to create the experience for us each year. Skilled programmers are constantly tweaking and improving the proprietary matching algorithm. Writers work tirelessly to write the invariably hilarious survey questions. The business team arranges sponsorships and partnerships to ensure that users have access to the free dates that bring the whole experience together. New features this year include Harvard-MIT cross- school dates, as well as the option to email the Cupids to ask not to be matched with an ex-partner, which has been a persistent problem. Datamatch is a labor of love by a very dedicated team, and it shows. The team also helps make the service available wherever people want it. Each year Datamatch spreads to more schools, and Harvard Datamatch helps each new location set up a team, implement the system, reach out to local sponsors, and write questions based on the subtleties of the school’s culture. According to Lee, “Datamatch will stop at nothing short of world domination.” This year they also rolled out a new survey to help freshmen meet other freshmen through the same data analysis that powers Datamatch. The survey of the upcoming year will be called Meet2024 and promises to become a Harvard staple in its own right.

Datamatch is a chance to reach out and make a connection without out any of the stress or the pressure. So, before this Valentine’s Day, fill out the survey, write a witty bio, and go get some waffles and see if there’s a spark.


Chidambaram Thillairajah ‘21 ( writes News for the Indy.