Have you ever used a dating app? If so, you’re not alone. Hundreds of millions of people use dating apps daily. Just in time for Valentine’s Day, CHM Live featured a panel of online dating experts from different eras, including Cofounder of Operation Match Jeffrey Tarr, Founder of Match.com Gary Kremen, and online dating consultant Steve Dean. The panel was moderated by Hanna Kozlowska, author of an upcoming book on the topic.
“We were two males in college who were very unlucky at dating,” explains Jeff Tarr, cofounder of Operation Match. It was 1965, and he was a 19-year-old undergraduate at Harvard. With money he’d won on a quiz show and a knowledge of IBM machines gained in a summer job, he and a friend launched a new endeavor. Offered at elite colleges in New England, Operation Match was originally a questionnaire with 75 questions that hopeful students could submit to have an “all-knowing” computer match them with a compatible date for $3.
Advertised by newspapers that would receive 10% of the take, Tarr received 7,800 responses. He and his partner paid to have them punched onto cards and rented service on an IBM 1401 during cheap off-hours to have them processed. Participants received 6 “ideal dates” and Operation Match was up and running. Improving the questionnaire and expanding across the country, the second version was wildly successful.
Jeffrey Tarr describes the popularity of Operation Match.
Operation Match worked on a simplistic basis, Tarr noted, nowhere near today’s dating apps. Of the 150 questions, they only effectively used 10 in the computer sort. But, there is plenty of anecdotal evidence that it worked—married couples still approach Tarr to thank him for connecting them.
When Gary Kremen was in his late 20s and a graduate student at Stanford’s business school, he was looking for dates through personal ads and 900 numbers without success. Good at computers and intrigued by how personal ads drove revenue for newspapers, he devised Match.com, the first and biggest online dating service.
The first incarnation, in 1993–1994, was based on email since few people had web browsers at the time. When the internet arrived, Match servers would go into overdrive during lunchtime because people could only access the web at work. At that time, more women were entering the workforce, people were marrying later, and everyone seemed eager to find a match efficiently. When Kremen realized there was a disconnect regarding profile photos—men wanted them, women didn’t—he decided to dig deeper.
Gary Kremen explains how talking to and hiring women improved Match.com.
Talking to women customers and bringing women into the company made Match.com better, with security features like blocking. Back then, the market was so huge that Kremen wasn’t worried about customer acquisition, even though he might lose two customers if the service succeeded so well that a couple dropped off when they committed to each other.
Steve Dean says that today's dating apps have made the cost of rejection very low, and users don’t usually leave an app permanently. Relationships often end after all. Lifetime user value is calculated not just on the initial period when a user joins the app but rather over the course of years. Often, a new user will burn out in first couple months because they’re using many apps at the same time, but after that wears off, they’re back on again. People clearly want to believe the apps work, but do they?
Dean believes dating apps have solved the problem of compatibility—delivering attractive matches—but a longer-term commitment that probably has a certain element of randomness is more difficult to deliver. Mobile devices and the ability to make profiles quickly has streamlined the industry. In 2012, Tinder collapsed everything down to four taps and a user could make a profile and get a match in seconds. That was unheard of at the time—the platforms required extensive questionnaires, and an eHarmony profile took 45 minutes to complete, for example.
But lately, dating app fatigue seems to be setting in. Dean is clear on the cause—the monopolistic Match Group and their addictive products.
Steve Dean says Match Group is causing dating app fatigue.
Match Group owns Tinder, Hinge, Match, Plenty of Fish, and countless other dating apps. Dean treats himself as a guinea pig, joining all of them and more so that he can see what people are experiencing. That sometimes involves messages coming in during the middle of the night trying to get him to engage. He takes screenshots of those and puts them in a folder he calls “Notification Hell.”
AI is now playing a role in the industry. Dean notes that it is now possible to be engaging only with an AI on a dating app, further reducing the human authenticity that people crave. On the positive side, some apps are adding AI that can help a user create a better profile or join in on a thread to help them flirt. As Gary points out, AI is like any other new tool or platform, and it can be used for good and bad. The tech is still in its infancy as far as helping to solve the business side of dating apps. Once it succeeds, we’ll see connection like we never have before.
So, hold on a little longer and you just might find that special someone!
Algorithms of Love | CHM Live, February 4, 2026
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