Inside The Online Matchmaking Industry’s Giant Blind Date

How eager young geniuses of love like the founder of plan to disrupt Big Relationship at the annual digital dating conference in Miami.

Inside The Online Matchmaking Industry’s Giant Blind Date

One guy says he can compute your “energetic compatibility” by punching the birthdates of you and your mate into an algorithm. When asked what information the algorithm takes into account, he shoots back, “Oh I can’t reveal that!” And then whispers: “It’s like our oracle.” Another guy insists he can predict your “mate value” by gauging facial characteristics, like the space between your eyes, apparently unaware that such dogma was discredited decades ago. The pleas and promises come fast and ardent: We can eliminate deception in online-dating! We can catch romance scammers! We have The Next Thing!


Welcome to Miami. The online-dating industry conference, an annual three-day affair, hosts a diverse mix of the date-o-sphere’s rich and poor. You’ve got the big corporate players (Google; Bing; and IAC, owner of Match and OkCupid); the geek-outsiders-cum-major-industry-disrupters (Plenty of Fish, Grindr); the pious marriage specialists; the purveyors of deviance; the upstart wannabes and the unabashed snake-oil salesmen. Some are too confident to brag or sell themselves. Others are too desperate or disillusioned not to.

Everyone thinks they’ve got a line on the future, a special sauce that will really “hit” in the coming year. It’s going to be all about free dating! Paid dating! Users want more privacy! Less privacy! It’s about leveraging the social graph! The interest graph!

In 2012, with a third of America’s 90 million singles dating online–not counting those who hook up through Facebook and other social-media sites–it’s easy to forget the recent bygone era, when “Internet dating” was considered a seamy, almost unspeakable underworld, where the web’s most troglodytic misfits sought weird companionship.

Yet past, as the poets say, is prologue. So it was a rather perspective-enhancing move, on the part of conference organizers, to kick off Day One with a keynote address from a congenial, awkward, and unassuming man, the original weirdo, Gary Kremen.
Seventeen years ago, Kremen, now 48, secured the domain-name “” from the government (when such was still possible), opened a small office in San Francisco’s South Park neighborhood, bought a $750,000 server on credit from Sun Microsystems, and launched what would become the Internet’s first mass-market dating site, a subscription-based service that promised, as the young Kremen reportedly put it at the time, “to bring more love to the planet than Jesus Christ.”

The exuberance was short-lived, however. In 1997, investor infighting over whether to make Match available to gays forced a sale to Cendant, a consumer-services company, for $7 million, of which Kremen walked away with a fraction. Eighteen months later, Cendant flipped Match–by then on its way to becoming one of the largest dating empires in the world–to Barry Diller’s IAC, for $50 million. “It’s difficult, giving up your baby like that,” Kremen told the conference audience. “I should’ve made the $50 million.”

It might be some consolation: all these years later, Kremen’s stamp is still very much evident, in at least one major way. Like its progenitor, most of the sites that followed Match guaranteed anonymity. You ponied up a picture and a written profile, but you didn’t reveal your actual identity until you wanted to. It was a stigmatized business, after all. What if your boss finds out!?


Today, though, everyone’s doing it. So, what if your boss finds out? Who cares?

In 2007, Alex Mehr and Shayan Zadeh noticed that the younger generation’s conception of dating was more closely described by a social-networking site like Facebook than by a traditional dating site. Online-dating seemed neither novel nor extreme to a generation that grew up online, nurturing social networks and watching each other’s lives play out in a cascade of relationship-status updates and Twitter news feeds. Privacy was something old people fussed over.

So Mehr and Zadeh launched Zoosk, a third-party dating application for Facebook. Zoosk allowed users to transfer their personal information over from Facebook. It had all the features of a social-network. You add people to your network. If they accept, then you can exchange messages with them and see their news feeds and photos. You nurture your network, chat via Zoosk’s messaging system, date some or all of the people in your network, and perhaps start a relationship. Zoosk, Mehr says, “is for a social life–with dating in mind.” By 2010, Zoosk had shot to the top of the U.S. rankings of online-dating sites, with nearly 5 million unique visitors.

Is the Match model dying? One of its former employees, who spoke to a packed conference room in the afternoon, believes that Match and its kind–i.e. traditional dating sites, which, by the way, currently account for most of the industry–have seen their day.

Brian Bowman used to be a VP of product development at Match. Now he’s taking them on with a new dating application called According to Bowman, the pay-to-communicate format established by Match in the mid 90’s resulted in a lack of innovation. Why? Because the business model Match spawned required anonymity. By limiting the amount of “real-world personal information” in profiles–i.e. Twitter handles, Facebook pages, etc.–a dating site can keep users on for longer. “Anonymity is a good thing when a person wants it,” Bowman said. “It’s not a good thing when it prevents someone who that person might like from understanding who that person really is.” Personhood can’t be captured in a simple database. You’re more interesting than that. You’re richer. You deserve better.

Rather than a static profile, will “tap into the sites that consumers use every day”–such as Netflix and Amazon–to create “a more dynamic interest graph.” It’s one thing to say you “like comedies,” “love to read,” “live for travel.” It’s another to show potential mates that your Netflix queue is full of Chevy Chase films, that you just bought you and your father copies of the latest Stephen King novel, or that your Picasa album has been updated with pictures from Peru. In Bowman’s vision, as Internet use rises, and people define themselves increasingly by where they go and who they talk to and what they post and buy–online–their dating profile evolves with them. “The first version of the Internet,” recalls Bowman, “was based around ‘It’–an index of linked websites that were interesting to most people, like Yahoo directories. Web 2.0 was based around ‘We’–me and my human relationships, my social graph. Facebook won that round. The next iteration will be about ‘Me’–who I am, my interests at this time, based not on what I say but on what I do.” As daters navigate the date-o-sphere, they’ll take their identities with them.


It’s a big change from the days of Gary Kremen. And the sort of transparency that contemplates (slogan: “It’s okay, be yourself.”) may make people uncomfortable. But that’s okay. Privacy, as Facebook founder Mark Zuckerberg has said, is a social norm that evolves. It also bears mentioning that many of online-dating’s problems–such as deception, and the time that an honest dater wastes by chatting up someone who turns out to be married, or twenty years older than their photo–stem from the privacy norm.

If online-dating culture advances to the point where the person you’re hoping to date has an expectation of transparency, or, in Bowman’s words, “authenticity,” openness will become the new norm. Privacy, as a trait or value, gets selected out. Zuckerberg was right. Morality may be divine but it’s also fickle. It shifts as the means of technology make new things possible.

Dan Slater is writing a book about the online-dating business and what technology means for the future of relationships, to be published by Penguin (Portfolio) next year. Slater is the founder and editor of The LongForum, a website that promotes the best of long-form journalism.

Click here for part two of this report from Miami, about the role of algorithms in the online dating industry. 

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