Why I’m dumping OkCupid’s blind dating app

OkCupid CEO Sam Yagan wants to bring back a vestige of the past: the blind date.

So we decided to give OkCupid’s new app, Crazy Blind Date, a whirl.

VentureBeat teamed up with ABC7 News reporter Jonathan Bloom for this project: I would go on an actual blind date, and the San Francisco network affiliate of ABC would interview my date on the spot.

See below for the video.

Setting up the app and the service is easy: Just download the free app on your iPhone or Android and connect to OkCupid if you’re already a member (or create a new account if you’re not). You’ll only need to reveal a few basic details: first name, age, whether you’re into men or women, and a profile pic, which the app will subsequently scramble (see left).

A word of warning: San Francisco is one of those cities where everyone knows everyone in their sector, particularly in the tech community, and the image scrambling is pretty easy to see through, so I was able to discern a few familiar faces when browsing the app.

Next, the app prompts you to create a date (“8 p.m. at Peet’s Coffee”). And then watch the offers fly in. Alternatively, you can browse a dozen or so existing dates and pick the one that’s most convenient. You’ll need to wait for confirmation from your potential date. Typically, this takes a few hours — if they respond at all.

My first impression? I was a bit underwhelmed by the sheer number of dudes whose ideal first date involves Dunkin’ Donuts or Peet’s Coffee. Step it up, people! Please!

After a few tries (my first blind date candidate never got back to me, and the second couldn’t meet up before 8 p.m.), I locked down a date with Bobby, a twenty-something with brown hair. His choice for the blind date impressed me: a taqueria in San Francisco’s Mission District known for its margaritas.

You can’t contact your prospective date until an hour beforehand, when the app lets you message back and forth. I received a note from Bobby confirming that he was actually planning to show up and informing me he’d be wearing a blue sweater.

Feeling duplicitous — ABC7 News was already on its way to televise the date — I ventured over to the restaurant. On route, I even considered writing down conversation topics on the back of my hand in case we had nothing in common. Bobby and I had arranged to meet at the bar. He gave me a quick hug, and I promptly informed him about the news crew waiting outside.

Bobby — aka Robert Leshner, the cofounder of Internet privacy company Safe Shepherd — took it like a pro. He’s startup guy, and is wise to the ways of the tech press. As it turned out, he had a bit of a heads-up about who I was. A few hours prior to our “date”, a mutual friend recognized me from my scrambled photo. Bobby had a feeling I’d be writing a story.

Three margaritas later, I was thoroughly enjoying myself, and I learned all about Bobby’s startup. Still, I’m unlikely to use the app again.

OkCupid may address some of my initial concerns over time. A few bugs prevented me from booking a last minute date — the app would tell me that “I’m already busy” on a particular night. I had to delete and reinstall it several times. And then there’s the chance someone might recognize you despite your scrambled photo. This is especially true for one of San Francisco’s thriving business sectors — the app’s “early adopters” are primarily tech folks. Not ideal if you’re in the startup world and want to expand your horizons.

Above: I met my blind date at a taqueria in the Mission.

Yagan is convinced the app will take off in time. To celebrate the launch, OkCupid went dark for a day, turning all of its profile photos black, so users would “have to make their dating decisions based on words and wits rather than abs and, well, other body parts,” the company said in a statement. In an interview with ABC7 (see below), Yagan claimed the app has already been used “hundreds of times.”

It’s a nice idea in theory, but when OkCupid introduced a similar blind dating service in 2007, it was a complete bomb. People weren’t all that comfortable meeting a complete stranger from the Internet with only a name, age, and scrambled photograph to go on.

I’m not surprised it failed. There is something both terrifying and awkward about going on a date with a mysterious stranger. Blind dates only seem to work out when it’s a set-up and you have a friend or two in common. Thankfully, Bobby and I had some common ground and could talk about tech, so we’ll end up as friends.

Check out my crazy blind date on ABC7. Online dating fans: Would you give Crazy Blind Date a shot?