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.

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?

This is a guest post by entrepreneur Alex Mehr.

Romance is a part of all our lives at one point or another – whether you are a casual dater, looking for love, or in a committed relationship. So it’s not surprising that an entire online industry has been created around romance. With the emergence of new technologies and the growing popularity of social networks, the online romance industry is constantly evolving.

While online dating remains a core piece of the online romance puzzle, social networking for couples has recently paved the way for a new business opportunity for entrepreneurs.

Singles versus couples

Traditional dating sites have been around for some time with great success. Recently, my business partner and I noticed a lack of opportunity for couples to interact with one another, and we launched a specifically designed product.

Since then, we have seen a growing trend of couples turning to private social networks to interact with one another. Additionally, we’ve seen a growing popularity around location-based social discovery services that are geared toward helping users find and meet new people in their vicinity. Each of these services plays a key role in the online romance industry as a whole.

The challenge, we realized, is that people’s relationship statuses change, which makes it difficult to keep customers long-term.

Since the early days of our company, Zoosk, customers would send us emails thanking us for helping them find love, sharing photos and the story of their relationship. One of my favorite stories came from a couple who met on Zoosk and then realized they lived down the street from each other. Even though they were neighbors, they never ran into each other before meeting online.

As customers continued to engage with our brand, even when they no longer needed a dating service, we saw an opportunity to overcome the challenge of customer retention, and created a service for people in relationships. This way, they’d have a place to share their stories – not just with us, but with their friends and family.

Companies must now offer different tools to users at every stage of their romantic journey. That way, when a user goes from A to B, it will be possible for them to easily switch gears and use a different set of tools more appropriate for that stage of their life.

Not only does this business model create more brand loyalty, but it helps eliminate the churn that is often experienced in the industry.

Private versus social

We live in a social world, both online and off. Yet, many of the services in the world of online romance are limiting to users because they don’t capitalize on social.

As I mentioned, several new services have popped up that offer private social networking for couples. These social networks are designed specifically for you and your significant other. However, we believe it is much more rewarding for couples to share their relationship memories and milestones with family and friends. With private social networks, the element of “sharing” is lost, and it’s easy to get bored. Isn’t it more entertaining when friends “like” and comment on your pictures?

I believe social networking for couples should be a core part of the online romance industry, but when developing a product, entrepreneurs must think bigger picture and incorporate more social elements.

Furthermore, in the real world, singles and couples are friends. They set each other up on dates and they wish each other “Happy Anniversary.” I’ve found that friends in a relationship often make the best matchmakers. Yet, many traditional online dating sites do not offer a platform that allows for those friends to give dating tips and advice to their single friends.

The evolution of social networking has made it possible for online romance sites to bridge the gap between friends, and even family, both single and in a relationship, by giving them the opportunity to be a part of one another’s romantic journey.

“Hookups” versus long-term engagement

Social networking services focused on location-based social discovery often get dubbed “hookup” sites. Depending on the service, that may or may not be true. Regardless, I like to think of it this way – every city has a bar that would be considered a hookup spot. So, it’s a given that the online romance industry would have its fair share of hookup spots.

This is an element of romance that has become a large part of the industry, especially with the proliferation of smartphones, and it will be around for a long time. But again, these services fill a specific need, and will lose customers as they move onto the next phase of their lives. Consequently, they will always have issues with long-term engagement.

Together, each of the elements of romance that I mentioned above makes up the online romance ecosystem. They represent the various stages of our romantic lives.

As an entrepreneur in the online romance space, I believe it is important to evolve with your users and to offer services that cater to each facet of their romantic journey, providing them with different tools and resources that will be useful every step of the way. While there is no doubt that the online dating industry alone has been incredibly successful, it is really just the beginning.

By expanding our services beyond dating, we’ve been able to create more brand loyalty and have also built stronger relationships with our users.

Alex Mehr (@alexmehr) is the co-founder and co-CEO of Zoosk, the romantic social network. He co-founded Zoosk in 2007 alongside Shayan Zadeh, while attending the MBA program at the University of California, Berkeley. Alex holds a Ph.D. in mechanical engineering from the University of Maryland. Prior to starting Zoosk, he worked as an engineer for NASA and collaborated on several manned and unmanned space flights.