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Founding the World's Simplest Dating Site

How about this: Propose a date; go on a date. No nonsense. Investors pounced, to the tune of $3.2 million. We caught up with the founders of HowAboutWe.com.
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Imagine Twitter had a dating service, where the only options were to propose dates, respond to dates, or directly message the person. A user could see the person's picture and basic information, and if interested, click a button to indicate that. Next: get a response, make simple arrangements, and—bam—go on a date.

That's not so far off from the service provided by HowAboutWe, an online dating start-up founded in November 2009 by childhood friends Brian Schechter and Aaron Schildkrout. The company, which is based in Brooklyn, New York, uses the tagline "get online to get offline."

"People love the idea," Schechter says. "Right now, overwhelmingly the response is, 'I get it! Finally a dating site that I'm cool to use.'"

With the industry's leading online dating sites, such as Match.com and eHarmony, users are required to fill out extensive profiles to be matched according to compatibility; then, after a bit of back-and-forth messaging, two users might just plan a date. HowAboutWe's proposal? Get straight to the dates to test for chemistry. The site works by presenting visitors a list of date proposals from singles from one or both genders in your immediate area. From there, users can click "I'm Intrigued," or send a message directly to the user. If the user responds back, all you have to do is pick a day, time, and not forget to brush your teeth.

The idea made a big splash at last year's New York Tech Meetup, where the founders pitched the idea, and drew a grand hush from the crowd when they noted that the user base was 60 percent female (to compare: 53 percent of all online dating service users are male). In less than a year since its launch, HowAboutWe has already had 100,000 proposed dates through its site. Acclaim, too, has been rolling in. The New York Times quizzed the founders this summer on the dating zeitgeist in New York City.

Most recently, some HowAboutWe members have proposed dates to meet at the TKTS booth to see a show; help out on a rooftop farm in Greenpoint, Brooklyn; try one of New York's 12 "most insane" new bacon dishes (as recommended by Eater NY); or enjoy a vegan dinner at Candle 79.

"You're connecting, you have this commonality already, but there's this element of exploration where you're not only meeting new people and finding people to go out with, but you're also doing things," says Erin Scottberg, HowAboutWe's media strategy director. "It's not stagnant, and it's not like sitting across from each other and talking about where we went to college and what our families are like, but you're doing something together, which actually makes the actual "going offline" part more natural than other dating sites."

Schechter hopes that HowAboutWe will help eliminate some of the the negative stigma surrounding online dating sites—which is not so much that they're inaccurate; just that they're, well, not cool.

"I think the online dating industry needs to be turned upside down on its head, because it's not providing people with the kinds of experiences that they want," Schechter says. "People are not excited or in any way prone to share about their online dating life with their friends right now—no one's like, 'Yes! I'm on this website! It's really cool!' in the way that they'd be excited to share that they're using Tumblr, or checking in somewhere on Foursquare, or finding a place through Yelp."

The cool factor has helped draw investment, too. Last summer, HowAboutWe raised a $3.2 million series A round led by RRE Ventures and joined by a broad syndicate of about a dozen investors, including Founder Collective, LaunchTime, and other angels. Yet, HowAboutWe still has a long climb ahead if it wants to catch up to its premier competition: Match.com produces over $340 million annually, and eHarmony reportedly makes over $250 million per year. While today's online dating industry generates over $4 billion per year, the average U.S. user of these dating sites is 48 years old. HowAboutWe hopes to broaden the appeal of online dating to reach the younger, more social media-savvy demographic.

"People have been saying for five years that online dating is in trouble with the rise of social networking, when in fact the more people become comfortable expressing their identity online—through Facebook, Twitter, and Foursquare—the more that there's usage of online dating sites as well," Schechter says. "I think online dating will continue to grow significantly."

For years, Schechter and Schildkrout—best friends since attending the same elementary school in Newton, Massachusetts—looked to launch a successful business together in hopes that one day, they would raise enough money to start a school. When Schechter lived as a teacher in Washington, D.C., he tried eHarmony on a prompting from Schildkrout's mother. While Schechter successfully found dates through the service, he found it to be a pretty embarrassing experience.

"It was always kind of awkward," Schechter says. "The context of the dates were pretty boring—a traditional dating site sets you up for cafe interview dates rather than something that's sexy and enticing. I did [eHarmony] for maybe a couple of weeks, and I was like, 'There's no way I'm going to meet the person I want to be with like this.'"

Schechter's impressions served as a basis for the partners' brainstorming: How could you provide a service for people to meet while avoid making it feel like a drag?

"We really pounded through all of our ideas and ended up with this eureka moment of, 'What if you have a dating site that's just a date that someone wants to go on?'" Schechter says. "How about we go see Shakespeare in the Park? Or how about we go to a cafe and play Scrabble, or play pool, or check out a lecture, or go to a museum I wanted to go to?' A specific activity, shown along with a picture of a person, so you can look at it, send an "I'm in" message, make a couple plans, then go."

Schechter and Schildkrout worked together to discover what's successful about today's popular social media and incorporate those features into a simple, streamlined dating site.

"There's some way in which Twitter, Facebook, and other applications that provide people with some utility in their lives, have begun arriving at a certain consensus about the structural dynamic of the user experience, in terms of posting, stream, navigation, and a very simple streamlined user experience," Schechter says. "Those are some of the things we apply when thinking about our design."

While HowAboutWe makes its daily money through its subscription service, the company also plans to develop sponsored listings from restaurants or venues on where to have a date, which would invite small businesses to capitalize through their dating service in a similar way to Foursquare. While HowAboutWe is primarily focused in five cities—New York City, Los Angeles, San Francisco, Boston, and Washington, D.C.—the company also plans to launch a mobile application this spring. The mobile app will allow singles from even more networks, both nationally and internationally, to get involved.




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