Online Dating Gets a Makeover

Aaron Schildkrout and Brian Schechter, Co-Founders, HowAboutWe online dating site

Though online dating sites have become decidedly mainstream, that doesn't mean it isn't often still a drag. The heightened self-descriptions, the awkward messaging, and, of course, those unbelievably bland first dates. Another boring round of meet-and-greet drinks and you are going to throw in the towel. Even if Mr. Across-the-Table isn't Mr. Right, it would at least be a better use of your time to do something more interesting than grab yet another beer.

That was the frustration facing Brian Schechter and Aaron Schildkrout, friends since elementary school who had always wanted to start a business together. As they reached their 30th birthdays, the issue of dull dates, was, as they say “a hot topic.” Tired of the typical online dating site scenario, they wanted a more natural, sexy, and fun way to enjoy the process. So they launched HowAboutWe, an new online dating site where users propose dates that begin with the line “How about we…” and end with anything from a "play a raucous round of ping ping" to "go trampoline jumping," to "play Scrabble at a coffee shop," to "attend a poetry slam."

HowAboutWe online dating site Homepage

Schecther and Schildkrout launched their new online dating site in New York one year ago on Valentine's Day and have since grown to 35,000 members in New York, Boston and Washington D.C. Los Angeles and San Francisco are adding members now.

Since love is certainly in the air this time of year, we thought it fitting to talk to the duo about their favorite HowAboutWe blind date stories and why showing up with a gift might not be a bad way to start things off.

The Inside Source: So, you two are in the business of first dates. What are the best first date stories you both have?

Brian Schechter: Oh wow. I was 22 and with my date I bought a dozen roses, grabbed two skateboards, and we rode down the street handing our roses out to strangers. That was pretty great.

Aaron Schildkrout:  Apple picking—but it wasn’t a first date. Maybe that’s why I started HowAboutWe. I’m looking for a much better first dating scenario, where I can have a better interpersonal connection.

The Inside Source: Does that mean you aren’t just the President; you are also a HowAboutWe member?

Aaron Schildkrout: Yes! I have a HowAboutWe date tonight to have Manhattan cocktails in Brooklyn.

Brian Schechter: Currently, I’m not. But, I did meet my girlfriend at a HowAboutWe event that Aaron and I hosted.

The Inside Source:  What would you say is your favorite thing about the first dates proposed on HowAboutWe?

Aaron Schildkrout: They’re all great. Some of them are fun and outlandish and some are really classic and simple. But the great thing is that people get to have a lot of fun on a date and be in on the process where finding love is not a drag. It’s not something where you sign up on an online dating site because you want to bite the bullet; it’s because you’re adventurous and you like to get out.

Brian Schechter: Couples who met through HowAboutWe dates email us all the time and tell us that their first date set the tone and the DNA of their relationship. They’re still continuing to do fun stuff. 

A couple on a HowAboutWe date—playing checkers

The Inside Source: What have been some of your favorite dates proposed on the HowAboutWe online dating site so far?

Aaron Schildkrout: Each date is unique and the best way to answer this question is to go on the site and see what people are currently proposing.

(And with that Schechter and Schildkrout pick up their iPhones and start listing in rapid succession dates that are currently being proposed on site)

Aaron Schildkrout: A Boston member is currently proposing, “How about we sneak Chinese food into the Brattle Theater and watch old movies while waving chopsticks to the soundtrack?”

Brian Schechter:: Here’s one: “How about we find a holiday market and a hot toddy?” A hot toddy sounds so nice right now!

Aaron Schildkrout: “How about we watch people ice skate at Bryant Park”

Brian Schechter: “How about we be rebels and have pie for dinner? It is savory pie so it’s not really that rebellious.”

The Inside Source: And since you launched the HowAboutWe online dating site last year how many HowAboutWe couples have blossomed? Any marriages?

Aaron Schildkrout: There have been hundreds of couples at this point. No marriages yet. But, wait until next year. Funny enough, many of our HowAboutWe lovebirds’ first dates were “How about we go shuffle boarding in Brooklyn.” That’s a great way to start a relationship!

at a candy store

The Inside Source: Alright, so you two know what can make or break a date. Let’s say I gave you eBay’s vast marketplace to create the perfect date ideas. What would you search for?

Aaron Schildkrout: I think women really notice shoes on men and I have bought shoes on eBay that I think have made all the difference.

Brian Schechter: A gift for someone on a date is such a great ice-breaker. Someone once got me a gift, a set of pocket tarot cards, and it was great.

Aaron Schildkrout: Gifts are fantastic. I like giving gifts especially. I wish I had a bunch of gifts just to pick up and bring on a date.  Like a great snow globe. It happens to be snowing and I have a date tonight. I’d love to show up with that.

Brian Schechter: I could also imagine bringing board games on a date. Like a vintage Boggle set.

Aaron Schildkrout: What about rubber cement? It’s the best thing out there for making art projects. And construction paper. And other art things.

Brian Schechter:  I wish I had shopped on eBay before dates more often!

wine tasting

The Inside Source: And finally, what has been your best Valentine’s Day date ever?

Brian Schechter: I used to work at flower shop. I got a discount through my store once on Valentine’s Day and well…

Aaron Schildkrout: Pool hopping at Boston hotels. We pretended to be guests and went from pool to pool. I wouldn’t suggest it as a first date. But probably a third date!

HowAboutWe founders Aaron Schildkrout and Brian Schechter shop eBay for first date supplies.

Vintage Board Game

Snow Globe

Art Supplies

Shuffle Board

Vintage Skateboard

Men's Shoes