Meeting expectations

Childhood friends from Newton have developed a dating site that is built around the dates themselves

By Taylor Adams
Globe Correspondent / December 9, 2010

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Q. What is

Schildkrout (pictured, at left): It’s a new way of dating. The way it works is people say: “How about we,’’ and then they fill in the dots with whatever dates they want to go on, connect with other users, and go out. The idea is to make it fun and easy to go on awesome dates.

Schechter (pictured, at right): The experience that someone has on our site is one of being asked out every day. There’s a daily e-mail of date proposals, and on your homepage there’s a stream of dates for you, selected based on your interests.

Q. Both of you are from the Boston area. How do you think your site meshes with the Boston social scene?

Schechter: When I lived in Boston, there were a ton of restaurants, activities, and cultural things that I didn’t always get a chance to do. People are using the site to go and do that thing they haven’t yet done, like go see the new wing at the MFA, or to check out a new restaurant that just opened up in Beacon Hill.

Schildkrout: People know their city, and they know what is awesome in their city, and what’s fun to do in their city, and they’re proposing those things. And in Boston, the dates are very Boston . . . the site tends to carry the local character of the people who are using it.

Q. How did you come up with the idea?

Schildkrout: We wanted to create a dating site that we would be excited to use and identify with. One that felt cool, one that felt like it matched the ethos of our generation, one that people would be happy to use and would tell their friends about.

Schechter: Aaron and I kind of represent the people that we’re going after. I had tried using an online dating site in the past, and found the experience laborious in terms of having to spend a lot of time filling out a profile; it didn’t seem productive or fun. It was just not the kind of way I wanted to meet people.

Q. Why do you think this is better than the experience on other dating sites?

Schildkrout: The emphasis on our site is what you’re going to do on dates and where you’re going to go, rather than — or in addition to — who you’re going to go with. There are still profiles on our site, but the primary way of interacting is around actual date ideas.

Q. What sorts of things are people coming up with?

Schildkrout: The way we want to answer that is literally just to go onto the site to a Boston area ZIP code, and see what the most recent dates are. Consistently, our experience has been that a huge percentage of the dates are awesome.

Schechter: How about we . . . go out for coffee, walk through the Public Garden and go ice skating at the Frog Pond? How about we go see a midnight show at the Improv Asylum? . . . How about we go for a 10-mile run together? . . . There’s one that says how about we go to Logan Airport and take the first flight available to depart?

Interview has been condensed and edited.

Taylor Adams can be reached at