A Stanford grad student created an algorithm to help his classmates find love; now, Date Drop is the basis of his new startup

As Valentine’s Day approaches at Stanford, some students may be preparing for first dates — not with people they found on Tinder or Hinge, but with matches from a service called Date Drop, created by Stanford graduate student Henry Weng. Date Drop pairs students with potential dates each week, using an algorithm that draws on their questionnaire responses.

A Stanford whiz kid trying to disrupt an established industry from a Palo Alto dorm? It’s a familiar storyline. But young adults are increasingly disillusioned with the frustrating, demoralising experience of modern online dating. So why not try a different approach?

Since launching in the fall, more than 5,000 Stanford students have tried Date Drop. The service has also expanded to 10 additional schools, including MIT, Princeton, and the University of Pennsylvania. Weng says he plans to broaden Date Drop’s rollout in certain cities this summer.

“Our matches convert to actual dates at about 10x the rate of Tinder,” Weng said. “Instead of swiping, we get to know each person deeply and send them one compatible match per week.”

Weng initially did not plan to build a startup around Date Drop. Then, one of his close friends met their partner through the service. “That was when I got the sense that this was less of a project,” he said.

Now, Weng says Date Drop is only the first product from his new company, The Relationship Company, which he set up as a public benefit corporation. This structure legally requires the company to consider social impact alongside profit.

“This started as something I just wanted to exist on campus, and it became a company because people kept on asking for it in their schools, and I needed resources to do that,” he said.

Weng has already raised “a few million” dollars from angel investors. Those backers include Zynga founder and early Facebook supporter Mark Pincus, who has taught business classes at Stanford and has taught Weng. Andy Chen, a former partner at Coatue, and Elad Gil, an early investor in Airbnb, Stripe, and Pinterest, also invested in The Relationship Company.

“The long-term vision at The Relationship Company is about facilitating all meaningful relationships: friendships, professional connections, community, events,” Weng said.

Algorithms have long been used to predict compatibility in dating services — that’s effectively the backbone of dating apps. But Weng says his model is designedforh long-term relationships, noting that 95% of Date Drop users say they are seeking relationships.

Weng describes two main pieces that make the system work. The first is building a questionnaire that is detailed enough to capture a meaningful picture of a person. “We do that through the questions, open-ended responses, a voice conversation, and other data that the users provide,” he said.

The second is predicting compatibility. “Because we help people plan dates, we have data on which matches actually work out. So we have a model trained on real-world outcomes,” he said. “Once you have those two components, the actual matching is standard stuff from matching theory literature.”

Weng is pursuing a master’s degree in computer science at Stanford and has structured his studies around economic and mathematical concepts in matching. As an undergraduate, he even created his own major focused on humans, matching, and incentives.

“I started to see how matching shapes so much of our lives,” Weng said. “Who your life partner is, who your friends are, what college you go to, and which company you work for are all matching problems.”

Outside of the technical side, Weng said an unexpected class helped him learn to manage a startup: “Intro to Clown.”

“A core principle of clowning is that clowns are failures, and instead of fearing failure, they revel in it,” he said. “As a product builder, your entire journey is just repeatedly failing and getting back up. Clown class was a wonderful microcosm of that.”

So far, The Relationship Company has two employees in addition to Weng, along with 12 students who serve as campus ambassadors. Since the company is built around forming connections, Weng said he has applied that mindset internally as well. Employees receive a $100 monthly “relationship stipend” that can be used on dates, gifts, experiences, or anything that helps deepen an important relationship of any kind.

“Relationships are the single most important factor in a person’s life,” Weng said. “There’s also great research showing that money spent on other people makes you happier than money spent on yourself.”

Weng’s interest in how relationships form has also shaped his day-to-day perspective.

“Date Drop has shown me how many interesting people are out there that you’d never encounter through your normal routines,” he said. “It’s made me more open to people I wouldn’t have crossed paths with otherwise.”