The Love Techs

Floyd's 99 Barbershop in the Back Bay is a chain, but it's a "hip" chain—hip in the sense that it occasionally plays hip-hop and the stylists are all young and have complicated asymmetrical two-tone haircuts. The clientele is young, too: Berklee kids in skinny black jeans getting faux-hawks, Urban Outfitted frat boys from Northeastern getting Growing Up Gotti–style blowouts. I didn't go to Floyd's thinking about dating, but it's nonetheless where I experienced an epiphany on the subject.

It began with my barber, Mike, a bearded guy whose good looks and laid-back nature made me think that if he lived in L.A. he would probably be a barber/actor. He was taking his clippers to the back of my neck when he started in on the success he's been having dating online. The receptionist chimed in to offer anecdotes of her own online dating adventures. A manager type looking on chuckled knowingly. And it was in the midst of all this innocuous small talk that I realized what was going on. I was in a normal, relatively cool place, having a normal, relatively cool conversation with normal, relatively cool people. About online dating. And that sort of freaked me out.

Rewind your social-judgment clock to Y2K, or even to just four years ago, before the proliferation of social networking sites, and try to remember who you thought dated online. A quick straw poll of my mom—ever the pulse of the mainstream—provides a refresher: "creepers, child-snatchers, and geeks." Harsh though that may be, what's true is true. But if you think it through, the shift toward acceptance that online dating has undergone feels almost inevitable. As a generation of computer-using kids reaches dating age, the idea that the Web is just as natural a tool for finding a date as it is for finding an apartment no longer seems so crazy. And that's not lost on Web entrepreneurs, who are finding good reason to tap back into what was not so long ago a maligned business: Experts project the suddenly booming industry could be worth more than $900 million annually within three years.

Such rosy prognostications, though, come at a time when analysts say interest in the industry Goliaths, sites like Match.com and eHarmony, has plateaued.

The growth is coming from upstarts, the most promising of which is plucky Cambridge-based OkCupid—a company hell-bent on changing everything you thought you knew about online matchmaking, and maybe matchmaking in general.

The site's founders—math-majoring Harvard alums Max Krohn, Chris Coyne, and Sam Yagan—seem an unlikely trio to change dating norms. But such are their not-insignificant ambitions. Borrowing the insights that made the social networking behemoths Facebook and MySpace so popular, their OkCupid eschews the standard playbook for online dating sites (for starters, theirs is free) in favor of the novel idea that they ought to be, well, fun.

That the three founders were also the creators of a once-popular online community, TheSpark, explains their approach a bit, or at least their intention, which is to provide a site where users can just hang out, click around, and meet some people. If that sounds to you like the same sort of environment in which people form connections offline, you'll perhaps understand why the site has more than half a million active users, and why OkCupid is creeping within striking distance of Match.com (which boasts some 1.3 million paid subscribers).

Nowhere is OkCupid more popular than here in Boston, where some 45,000 use it. Popularity like that not only makes sense—we are, after all, a city brimming with college kids and busy young professionals with serious tech know-how—it also explains the chatter at Floyd's.