The 'grandfather of online dating' reveals the 3 crucial questions that can predict long-term compatibility in a relationship

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Sam Yagan is colloquially known as the “grandfather of online dating.”

He founded OKCupid in 2003 with some friends whom he met while attending Harvard University, where he had started SparkNotes, a study-guide company. Yagan later went on to become the CEO of Match.com and also spent time as a director at Tinder, a product of Match Group, which also owns OKCupid, PlentyOfFish, Tinder, Hinge, and Match.com.

When he was starting OKCupid, Yagan said he and his friends were looking for a different solution to online dating, one that used mathematics and substantive data to predict compatibility.

“We basically said, rather than us try to figure out how people should date, let’s basically try to create a model, an algorithm, that models the real world,” Yagan told Business Insider in a recent interview.

As such, Yagan and his business partners designed a website with a question-and-answer-based system to help people determine whom to date.

What he found when he looked at the data was somewhat surprising.

“You can disagree on religion, you can disagree on pets, you can disagree on lots of things,” Yagan said, explaining that three specific questions were the best predictors of long-term compatibility in a relationship.

Yagan is currently taking a break from the online dating business as the CEO of ShopRunner, a service that partners with various retailers to provide free two-day shipping. But ahead of Valentine’s Day, he told Business Insider the three main questions that could predict whether a couple would last, according to data from OKCupid.

Here’s what they are:


1. Do you enjoy horror movies?

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While this question might seem random, Yagan offered some insight as to what it could say about a person.

“The idea of a horror movie, the idea of going and scaring yourself, is some deeply innate thing,” he said.


2. Have you travelled alone in a foreign country for fun?

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“Travelling alone in a foreign country to me is like the most horrible possible thing I would ever want to do,” Yagan said.


3. Have you ever wanted to chuck it all and live on a sailboat?

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Yagan said he’d answer no for all three questions, though he’s never had to do so in an online dating platform – he married his high school sweetheart and never used any of the dating services he created.