As Valentine’s Day approaches at Stanford University, some students may be preparing for their first date. Rather than someone you met on Tinder or Hinge, you’re going on a date with a service called Date Drop, created by Stanford University graduate student Henry Wen. Date Drop pairs students with potential dates once a week based on survey responses.
Is a Stanford University genius trying to disrupt an existing industry from his Palo Alto dormitory? If you’ve heard this before, stop it! But young people are deeply disillusioned with online dating’s frustrating and demoralizing conditions. Why not try something different?
More than 5,000 students at Stanford University have tried Date Drop since its fall launch. It has also been rolled out at 10 more schools, including MIT, Princeton, and the University of Pennsylvania, and Wen said he hopes to roll out Date Drop more broadly in select cities this summer.
“Our matches convert to actual dates about 10 times faster than Tinder,” Wen told TechCrunch. “Instead of swiping, we get to know each person deeply and send them matching matches once a week.”
Wen didn’t initially intend for Date Drop to be the foundation of his startup. Then a close friend of his met his partner through a date drop. “At that time, I felt like this wasn’t a big project,” he says.
Wen now sees Date Drop as just the first offering of his startup, Relationship Company. Relationship companies are public benefit corporations, a type of company that is legally required to consider social impact alongside profits.
“This started out as just wanting to have a presence on campus, but it became a company because people kept asking for it in their schools, and we needed the resources to do that,” he said.
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Wen has already raised “several million dollars” from some angel investors, including Mark Pincus, founder of Zynga and early Facebook backer who taught business courses at Stanford University. Andy Chen, a former partner at Coatue, and Elad Gil, an early backer of Airbnb, Stripe and Pinterest, are also investors in the relationship company.
“The Relationship Company’s long-term vision is to foster all meaningful relationships, including friendships, professional connections, community, and events,” he said.
It’s no surprise that users of dating services use algorithms to predict whether or not they’re compatible with each other. That’s how dating apps work. But Wen says his model is more focused on building long-term connections, with 95% of Date Drop users saying they’re interested in relationships.

Wen explains that there are two central elements at play. First, the survey needs to be thorough enough to get a true picture of the person. “We do that through questions, open-ended responses, voice conversations, and other data that users provide,” he said.
The next challenge is predicting compatibility. “We help people plan their dates, so we have data on which matches actually work. So we have models trained on real-world results,” he said. “Once you have these two components, the actual matching becomes standard in the matching theory literature.”
Currently pursuing a master’s degree in computer science at Stanford University, Mr. Wen’s education has focused on the economic and mathematical concepts of matching. As an undergraduate at Stanford University, he founded his own major studying people, matching, and incentives.
“We started to realize how important conformity of form is in so many of our lives,” Wen told TechCrunch. “Who your life partner is, who your friends are, what university you go to, what company you work for, everything is a matter of matching.”
Beyond technical education, Wen discovered unexpected classes that helped her learn how to run a startup. It is “Introduction to Crown”.
“The basic principle of clowning is that clowns are failures, and rather than fearing failure, they enjoy it,” he says. “The journey as a product builder is one of failure and recovery, and Crown Class was a great epitome of that.”
So far, The Relationship Company has two other employees in addition to Wen and 12 students who serve as campus ambassadors. Since their work revolves around forging matches, Wen extended that philosophy to the way the company is run. He offers his employees a $100 monthly “relationship allowance” that they can spend on dates, gifts, experiences, and all sorts of other things that help deepen important relationships.
“Relationships are the most important element in life,” Wen says. “There’s also some great research that shows that spending money on others makes you happier than spending money on yourself.”
Wen’s interest in how people form relationships also influences the way he conducts his daily life.
“Date Drop showed me how many interesting people there are in the world that you would never meet in your normal daily life,” he said. “It has allowed me to be more open to people I would not have met otherwise.”
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