HowAboutWe: Dumbo couples dating startup expands to Chicago and Seattle

If you want to take your partner on a nice date but don’t have any good ideas about what to do or where to go, HowAboutWe will plan it for you and save you money when you go.

At least, if you’re in New York or San Francisco, and — as of this morning — in Chicago and Seattle as well. The Dumbo startup has employees on site in both cities now and is continuing to hire more.

Couples pay a monthly fee for access to dates that the site staff negotiate with local businesses. In many cases, HowAboutWe customers get discounts of as much as 50 percent and, in some cases, will include little touches exclusive to HowAboutWe dates.

For example, when you get your customized sandwiches from Manhattan’s Peanut Butter & Co. through the site, they will each come out with little hearts on top. While you complete the purchase of the packaged dates through the site, the company doesn’t keep any of the money. The negotiated price goes wholly to the business, while HowAboutWe earns its revenue from subscriptions.

• The four year old website’s tagline is “Fall In Love / Stay In Love.”
• It started as a dating site that expanded into a couples service.
• Its big innovation was that it was focused on getting potential partners offline.
• Schechter founded the site with Aaron Schildkrout, 34.
• They started working on the idea in Boston, but launched it from Brooklyn.
• Its first employees worked at Green Desk, before the operation moved to 20 Jay St.

In 2010, dating sites weren’t focused on dates, Schechter says. They were focused on extensive searching, involved profiles and messaging. According to the cofounder, if you talk to an OKCupid user, you will hear that people exchange eight to fourteen messages before they ever meet up.

On HowAboutWe, singles introduce themselves by posting date ideas. So, if you’re scanning available people on the site, you’ll see a photo of a person and next to it a box will say something like, “How about we… get fro-yo at Yogumoo and then take a walk through the Botanical Garden.”

It allows users to show what neighborhood they’d like to go out in, without showing exactly where they’d live. The site has recently added a function that lets you see these date ideas on a map.

Schechter explained that once people started coupling up, they began to write in to the founders saying that they wanted to keep getting date idea emails, but they didn’t need suggestions of who to go out with anymore. Which led to creating the couples side of the site.

Shechter said that, in a way, other dating sites have a disincentive to helping people actually find a partner. They profit from eyes on their websites, and there is a lot of churn in the dating space as people actually do find partners.

The couples focus allowed them to continue their relationship with people who came into the site through the singles side. For $18 per month, a couple gets access to dates in the site’s date book, including one free date per month.

The company closed a $15 million Series B round in 2011. Asked about their intention to seek additional investors, Schechter said the company is focused on continuing to grow its user base now.

Here are some more photos from inside the company, which has grown enough that it may have to vacate its space at 20 Jay Street in Dumbo.

Brian Schechter with the Development Team behind him

The next two photos are of the direct marketing and design teams