The Love Techs

If OkCupid is like a bar, it's one of those Faneuil Hall places where the shots come in test tubes. In other words, it's set up to cater to the post-college crowd. In itself, slicing the online dating pool into easy-to-reach niches is hardly new. But going after younger daters is. Whether by race (BlackSingles.com), religion (popular Jewish site JDate), or gold-digging tendencies (Sugardaddie.com), plenty of websites are tailored to a specific audience, yet even within those populations the target customer is generally older.

This is understandable, since a) older people are more likely to run with a smaller crowd, thereby exhausting real-world dating options more quickly, and b) they're suckers when it comes to paying for things on the Internet. It's in a nod to this demographic that Match.com has made Dr. Phil the face of its site, signing him up to provide users with rhyming relationship advice. The well-advertised eHarmony, meanwhile—which markets itself as creating matches for people serious about finding marriage material—combines a socially conservative agenda (gays and daters with more than one divorce need not log on) with an extensive screening process involving so many essays and hourlong questionnaires that one former user told me the experience was a lot like filling out college applications and taking the SAT—at the same time.

The young daters OkCupid is after (Yagan says the company imagines them to have an average age of 26) arrive at the site expecting that the services they get online are not just free, but entertaining as well. Knowing that, Yagan and his cohorts have tried to re-create what works in the real world, and also what they've seen work elsewhere on the Web. On top of must-haves like the all-important profile pictures and the ability to flirt with other users (in OkCupid's case, by sending a "woo"), their site allows you to mix with others in some pretty unique ways. Its new Wikiprofile feature, for instance, lets you edit a friend's bio, changing his interest in the Rolling Stones to, say, Hannah Montana. Not only does this provide hours of laughs, it's also an ingenious way to force users to stay active on the site, lest their defaced profile cut into their woo count. OkCupid is a Web space where irreverence is the lingua franca. (Want to see who's viewed your profile? Click on "My Stalkers.")
As we walk out of Legal Sea Foods and into the cold Cambridge air, Krohn points out the Gehry-designed building where he studies, then stops and chuckles.

"You know what I was just thinking about? Five years ago, you could almost see yourself going to Yahoo and saying, ‘I want to pay 10 dollars more a month to get 10 more megabytes for a 20-megabyte mailbox.' And now you go to Google and you get a five-gigabyte mailbox completely free." It's the theme of perpetual technological innovation in a still-young Internet era. And it's a story line that OkCupid fits into.

"Businesses just need to find a way to make money," Krohn says. "It's a new, completely different world. We understand that; Match.com doesn't. We just hope it's going to be us that takes them down."