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This article was published on January 26, 2011

HowAboutWe makes online dating fun again

HowAboutWe makes online dating fun again
Courtney Boyd Myers
Story by

Courtney Boyd Myers

Courtney Boyd Myers is the founder of, a transatlantic company designed to help New York and London based technology startups gr Courtney Boyd Myers is the founder of, a transatlantic company designed to help New York and London based technology startups grow internationally. Previously, she was the Features Editor and East Coast Editor of TNW covering New York City startups and digital innovation. She loves magnets + reading on a Kindle. You can follow her on Facebook, Twitter @CBM and .

The online dating world is heating up, but a lot of the big love-finding websites like eHarmony and Match are smelling pretty stale. HowAboutWe has the right attitude and is making online dating fun again.

Located in Brooklyn, New York, HowAboutWe is “all about wonderful people (like you) going on awesome dates. Playful dates. Cultured dates. Magical dates. Surprising dates. You say, “How about we…” and fill in the dots with the dates you want to go on.”

HowAboutWe works like this: Members fill out a profile, upload a photo and propose an intriguing first date idea. Other users browse proposed dates, and if they like what they read, they can message their potential date. “Partakers can design both an elaborate or simple rendezvous, from meeting for coffee or sampling sushi to conducting a couples séance in hopes of connecting with childhood pets.”

The site includes the traditional features of dating websites, such as online chatting, emailing, and profile cruising but HowAboutWe puts the emphasis on stepping offline to encounter real-life camaraderie. One of the service’s best features is the Daily Dates email with date proposals selected to match your profile; it’s a gold mine of interesting things to do in New York City. And the locations are conveniently powered by Foursquare.

The site’s emphasis on friendship is unique; it asks if you’d like to pull in your contacts from Facebook, Gmail and Twitter. You can also answer a list of questions so users can know a bit more about you like “The movie I’ve watched the most times,” and “An awesome place I’ve visited.” It also asks you to pick which dates you like or don’t like to weed out potential football watching afternoons.

HowAboutWe’s co-founders Aaron Schildkrout and Brian Schechter grew up down the street from each other; they even threw a 4th grade dance party at their elementary school together. The two became teachers in their 20s, then turned 30 and decided they wanted to start a big, exciting business, something a bit more challenging. After traveling together, they arrived at the HowAboutWe concept in August 2009. “We were both single at the time. What would would be cool in the States? What if you had a stream of date ideas?” says Brian.

With little background in either tech or business, Aaron and Brian have been learning along the way. They incubated the idea in Boston, from August to December of 2009 and launched the site one year ago in February 2010 in NYC. The site now has 35,000 users, 60,000 proposed dates and a crowding cadre of HowAboutWe couple stories.

“I’ve been thinking constantly about dating and the Internet. What it’s like for people to find love and meaning and having to engage in a digital culture, and how that translates into their real life. People have a hard time presenting who they are in a digital context and how they are in real life. HowAboutWe gets people off their computers and gets them together with likeminded folks who may want to protest at the UN together or explore Red Hook.” – Brian

Last month, HowAboutWe had an incredibly successful Groupon sale and dealt with Match totally copping their style after releasing a feature called “Date Spark.” It was also named one of the top dating sites by Boston’s The Professional Wingman. Signing up for the site, proposing and receiving dates is free but it costs $28 per month for advanced features like unlimited messaging.

With an iPhone app in the works, national offices in Boston and D.C. and a growing user base in San Francisco, London and Canada, HowAboutWe’s founders Aaron and Brian are prepping for a very exciting 2011. And what are their plans for Valentine’s Day?

“Honestly? No plans yet! I’ll probably dig into our stream of date proposals and pick one out!” says Brian.

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