How About We… Start An Online Dating Company?

A dating site that helps users go on more dates seems like a no-brainer. But it’s not that easy.

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Sandi, 36, a Los Angeles-based music executive, began looking for dates through the new online service HowAboutWe. The idea is that users finish the statement by proposing a date, like “How About We… go bowling?” But instead, she saw this: “‘How About We… I am looking for a person I can be honest with, do you think you can be the one?’”

This misunderstanding may be inevitable, given online dating’s traditional emphasis on pairing people according to personality. Anyone who has used a service like eHarmony or Match knows the drill. First you fill out extensive questionnaires, peruse extensive profiles, and exchange endless emails to figure out if you might hit it off in person. And then you wait forever to be asked on a date, worrying that you’ve mistakenly signed up for a pen pal service. In contrast, HowAboutWe asks users to provide minimal profile information and focus on proposing and responding to dates instead. In short, the site is trying to minimize the online aspect of online dating.

This is an industry—online dating, that is—that was worth $1.049 billion in 2010, and is projected to exceed $2.5 billion by 2015. So alongside heavy hitters like Match and eHarmony, countless niche sites are trying to reap the profits as well. If faith is important, try JDate or Christian Mingle. Like plus-sized romance? Check out Overweight Date. In fact, online daters can join sites targeted toward specific ages, ethnicities and lifestyles ranging from athletic to kinky.  What they all share is the idea that users will meet partners based on a predetermined preference or value. HowAboutWe is the first to encourage users to put actual dating ahead of these preferences.  

Since its national launch in December 2010, its users (average age of 29-35), have proposed over 300,000 dates, everything from day hikes to the proverbial drink. The site was founded by childhood friends Aaron Schildkrout and Brian Schechter who had turned 30, realized they were single and decided to do something about it. According to the website, “They built HowAboutWe as the dating site to match the ethos of today’s generation.”

That ethos involves more relaxed dating interactions. Allie, 32, an editor from New York, says, “It seems far more approachable and less awkward than traditional dating sites. Even OKCupid, which is really casual, didn’t feel this playful and laid back. But not playful in a ‘looking to hook-up only’ kind of way. Instead, taking it less seriously, laughing about it.”

But the biggest desire that HowAboutWe taps into seems to be ending those aforementioned drawn out email exchanges.

Says Jen, 36, a yoga teacher and writer from Los Angeles, “When you spend all that time emailing back and forth, you feel like you know someone, but you don’t. You don’t know how they carry themselves, if they’re confident. Then, when you finally meet and there’s nothing there, it can feel more awkward. And anyway, how much do you really need to know about a person before you meet them?”

While Jen has gone on dates much faster than she has with other sites, she notes that there don’t seem to be too many guys who have fully signed up and are able to send messages and accept dates. (While HowAboutWe is free to search, users must pay a monthly fee to contact other members.)

Some have found not only the numbers lacking, but the quality as well. Sandi, the music executive, was not only put off by guys who couldn’t properly fill in the blanks of the HowAboutWe form, but also by some of their user names: “Ursultry,” “dbest4real” and “ArtisticFuck.” Nor did she respond to the gentleman whose idea of a date was giving him a massage.

Yet Sandi is still enthused about the site’s dating-based concept. “Even if there’s no romance, at least you’re doing something fun on your date rather than just sitting at a coffee shop judging each other,” she says.

If HowAboutWe succeeds, it may mean that online daters have grown tired of falling for web-based personas, only to be disappointed by the people behind them. If instead HowAboutWe goes the way of Friendster, then perhaps the ultimate draw of online dating isn’t going on dates, after all. Maybe we turn to dating websites because we want to believe that finding our ideal mate is as easy as applying an algorithm.   We keep going back because that elusive soulmate who shares our enthusiasm for pina coladas and getting caught in the rain may be just a log in away.

Maybe we’ll never get over the thrill of asking virtual strangers if they think they can be the one.

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