Stanford Grad Student’s “Date Drop” Aims to Revolutionize College Dating with Algorithm-Driven Matchmaking

As Valentine’s Day approaches at Stanford University, some students are ditching the swipe culture of Tinder and Hinge for a more curated approach to romance. Enter Date Drop, an innovative matchmaking service created by Stanford graduate student Henry Weng that’s quickly becoming the talk of college campuses nationwide.

From Dorm Room Project to Multi-Million Dollar Startup

What started as a simple campus experiment has evolved into The Relationship Company, a venture-backed startup that’s already raised “a few million” dollars from high-profile investors including Zynga founder Mark Pincus, Coatue’s Andy Chen, and early Airbnb, Stripe, and Pinterest backer Elad Gil.

The numbers speak volumes: Over 5,000 Stanford students have tried Date Drop since its fall launch, with the service now expanding to 10 additional prestigious institutions including MIT, Princeton, and the University of Pennsylvania. Weng has ambitious plans to roll out the service in major cities nationwide this summer.

The Problem with Modern Dating Apps

Weng’s timing couldn’t be better. Young adults are experiencing unprecedented dating app fatigue, with studies showing widespread disillusionment with the swipe-left, swipe-right culture that has dominated digital romance for the past decade. The frustration is real—endless scrolling, superficial connections, and the paradox of choice have left many Gen Z users craving something more meaningful.

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

How Date Drop Works

The service operates on a simple but revolutionary premise: quality over quantity. Rather than overwhelming users with endless options, Date Drop sends each user one carefully curated match per week based on comprehensive questionnaire responses.

The questionnaire goes far beyond basic demographics and interests. It includes open-ended responses, voice conversations, and various data points that paint a holistic picture of each user’s personality, values, and preferences. This depth of information allows Date Drop’s algorithm to make connections that superficial swiping simply can’t achieve.

A Public Benefit Corporation with a Mission

What sets The Relationship Company apart from typical venture-backed startups is its status as a public benefit corporation. This legal structure requires the company to consider social impact alongside profits—a fitting choice for a business dedicated to fostering meaningful human connections.

“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,” Weng explained.

The Science Behind the Matches

Weng’s approach is rooted in matching theory, a field of economics and mathematics that studies how individuals and entities are paired in various contexts—from college admissions to organ donation to romantic partnerships.

“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,” Weng said. “Once you have those two components, the actual matching is standard stuff from matching theory literature.”

The results are impressive: 95% of Date Drop users report being interested in relationships, suggesting the platform is successfully attracting people serious about finding meaningful connections rather than casual hookups.

An Education Tailored for Entrepreneurship

Weng’s academic journey at Stanford has been anything but conventional. As an undergraduate, he created his own major studying “humans, matching, and incentives.” Now pursuing a computer science master’s degree, he’s oriented his education around the economic and mathematical concepts that power his startup.

But perhaps the most unexpected influence on his entrepreneurial journey was a class called “Intro to Clown.”

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

Building a Culture of Connection

Even within his own company, Weng is practicing what he preaches. The Relationship Company offers employees a $100 monthly “relationship stipend” that can be spent on dates, gifts, experiences, or anything that helps deepen important relationships of any sort.

“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.”

The Future of The Relationship Company

While Date Drop is the company’s flagship product, Weng envisions a much broader mission. “The long-term vision at The Relationship Company is about facilitating all meaningful relationships: friendships, professional connections, community, events,” he said.

With just two full-time employees besides Weng and a team of 12 campus ambassadors, the company is lean but ambitious. The combination of algorithmic matchmaking, human-centered design, and a mission-driven approach positions The Relationship Company to potentially reshape how young people form connections in the digital age.

Personal Impact

The success of Date Drop has even changed how Weng approaches his own social life. “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.”

As Valentine’s Day approaches, Stanford students—and potentially young people across the country—may find themselves trading the endless scroll for a more thoughtful, algorithmically-enhanced approach to finding love. In an era of dating app fatigue, Date Drop might just be the breath of fresh air that romance needs.

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