Dating Sites – Putting the Date Back in Dating

It’s been a long time since Brian Schechter and Aaron Schildkrout carried their elementary school dance parties. After 20 years of talking about “creating something that would shatter conventions and erect something way better”, these two childhood best friends came up with their best idea so far: HowAboutWe, an exciting and fun new way of dating.

In a time when dating site clones pop up in the hundreds, HowAboutWe.com introduces a different approach: instead of screening through profiles, you chose people based on their date ideas using a “How about we…” template. Members still fill out profiles but the action is all about the proposed dates. Can it get better than that?

By the time this article went out, these were the most popular dates on the site:

– How about we… have dinner at an underground supper club led by a secret famous chef.

– How about we… check out a scavenger hunt at the Met.

– How about we… walk the High Line.

– How about we… go for a walk, sit in Union Square and watch people.

I sent Brian a set of questions and here is what he has to say.

How did you get started and what inspired the idea of a dating site based on proposed dates?

We’ve been best friends most of our lives. We’re talking kindergarten on. And we always talked about creating something that would shatter conventions and erect something way better – way more real and way more fun. The range of our projects spans 20 years – from elementary school dance parties to lesson plans for high school students; we were both teachers after college. We got started with HowAboutWe last August (2009). We had decided we wanted to build a big business that would make people’s lives better and help people to do what they already want to do. We had tons of ideas but HowAboutWe was the best one. We were both single and the second we had the idea it was obvious that a site based around the dates people would want to go on would be the type of site we’d actually want to use.

What is HowAboutWe?

HowAboutWe is about putting the date back in dating. You say “How about we…” and fill in the dots with dates you’d have fun going on. Magical dates. Simple dates. Wild dates. Lovely dates. Each day we’ll send you new dates that match your interests. And, of course, we’ll send the dates you propose to people who might like them. Then you can check out people’s profiles, message each other, and go out. We think people are at their best when they’re doing things they really like to do. That’s what HowAboutWe is all about.

What’s the age range and the men/women ratio?

24-44-ish…45/65-ish.

What’s the best way to get a date on HowAboutWe?

Propose dates. Propose the dates you want to go on.

What’s the best way to NOT get a date on HowAboutWe?

Taking it too seriously.

What have you learned so far?

People are far more game for exploration, discovery and honesty than we had imagined.

Have you found any tendencies in both, men and women when proposing dates?

Women are more creative, have better vocabularies and are more specific.

You are based in New York. Is HowAboutWe intended for NY or US only?

No, we plan to grow on a national scale. We imply wanted to create a new kind of dating site where members could demonstrate who they are, not with personal essays and awkward messages, but by proposing dates that begin with the words: “How about we….”. We are beginning to expand.

How are you promoting the site?

We’re basically focused on creating an amazing site. The users of HowAboutWe tell their friends about it. Those friends tell their friends. That’s been the driving force behind our growth so far.

How do you plan to make money?

The site is a subscription service. People pay when they begin composing messages to other users.

How does a new dating site compete with the already established dating sites giants in a saturated market?

By having a good idea for making it different.

Are there any stories on the site you want to share?

One of our users, Lucinda, volunteered to go on 10 HowAboutWe dates…and write about each one. She recently dished out on one of her dates for our Date Report which is pretty comical and gives you a glimpse into the trials and tribulations of NYC dating.

As Lucinda puts it, “The best part of dating in New York is the mystery and the idea that anything can happen, love can find you anywhere.”

So be sure to propose a good date (hint: the dates that get the most responses seem to be ones that have a bit of personality), check your grammar since spelling mistakes are a huge deal breaker and be ready to go out and have fun.

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