NiteTalk: Founders Create Dating “Playground” for NYers

Nicole Wasilewicz

Founders Aaron Schildkrout and Brian Schechter celebrated along with eager daters at HowAboutWe's first official happy hour last week, after the launch of the new online dating platform at downtown's Sweet and Vicious. The entrepreneurs and best friends since kindergarten have created what Aaron's mom calls a "playground" for single people living in New York City -- where there's more than just late-night shenanigans to impress the opposite sex.

Niteside got a chance to talk with Aaron and Brian about the worst date spot in NYC, how isn't just for single people and that they're hoping business might set them up with a few eligible bachelorettes of their own.

What are you guys trying to accomplish with HowAboutWe?

Brian: We're trying to create an online dating site that we would actually want to use. Currently online dating is viewed as the option of last resort, and because of that it's basically assumed that online dating sites are lame. We want to create a non-lame dating site that people chooses to use and not because they have to, because they want to, because it's fun, it's engaging, it's creative, and it's an opportunity to meet new people and do things that you might not normally do but you really actually want to do.

Aaron: So, I hate, despise dating advice. I feel like whenever I read dating advice, it's like somebody is putting a prescription on my dating style, which is the antithesis of our conception. We wanted a site that's free, where people do what they want to do and not get cheesy advice about the top ways to do X, Y, or Z. ... People should be themselves and that's the most effective thing you can do in the dating world.

Do you feel like New York City is the perfect playground for what you're doing?

A: New York City makes perfect sense for HowAboutWe because it's about what our users want to do, and New York is filled with opportunities from theaters, bars and restaurants to cafes, parks, etc.

When it comes to nightlife, where do you think are some of the best dating spots in the city?

B: I think it depends on your personality, like, there's not one particular place people should go to because it has a distinct vibe since each individual has their own vibe too. What we've been seeing a lot of is your usual dates like wine bars, cafes or just going for a walk. But then there's people who want to do more funky things like paintball, go to Staten Island, do the trapeze show, take a kung fu class -- and the beauty is that New York offers all of those things.

What would your perfect date be?

B: Going to a wine bar where it's not too loud and the vibe is sexy -- that's pretty standard. I think the multi-phase date is great -- where we could start off at a vintage clothes store, and then afterwards we can see if we want to get a drink and then having in my mind a show or something to see afterwards if the drink went well.

Outside of the dating spectrum, what are some places you love to go to when you're out and about?

B: Definitely have to give some props to Sweet & Vicious and The Richardson in Williamsburg. The Snakehead, which is in our neighborhood and Les Enfants Terribles are places that we hang out often. Also, White Star sometimes. Right now we're very concerned with the launch of the site so local bars are our thing, which aren't always the best places for dates anyway.

A: Late night at the dumpling shops in the Snakehead, which is what we call where the Lower East Side meets Chinatown. Every one of those places is bad for a date but a great place to go late at night. Well, actually, that kind of highlights what's so great about HowAboutWe because if you found someone who was really game for that, then you found your perfect date.

So why did you decide to go forward with HowAboutWe? Where did the idea come from?

B: Well, a date proposal is just much more reflective of what someone is actually like rather than a traditional dating profile because it refers to something that they're ready to do right now, so it lends itself to a way of meeting someone that is more natural.

A: As my mom said at the launch of the site, when I was very concerned with the features and stuff, she goes, 'Aaron, all you're doing is creating a playground for people,' and I agree with that. It's basically a space where people can do what they want to do, they can propose the dates they want to propose, they can say what they want to say -- so it's basically a space for people to generate the lives they want to generate.

B: When people do that, when they have a community that supports them to just say who they are and what they're about, immediately what's great about them comes through.

Is there a subconscious factor that's pushing you, like possibly getting dates for yourselves?

Both: It's not subconscious. [laugh]

B: We would have never of done this if we were both in committed and content relationships I don't think. But the truth is that HowAboutWe is not just for single people.

A: Yeah, I mean the date ideas are great for couples too. We want people in relationships or who are married to come to the site to see what they could be doing together.

Where's the worst possible place to go on a date in NYC?

A: Is there an IHOP in NYC? There's one in Brooklyn, right? Worst date spot definitely. There are just too many opportunities for people to make mistakes by ordering Buffalo wings or blueberry pancakes.

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