TheGloss is excited to have begun a partnership with HowAboutWe – a dating site that matches you up based on dates you’d like to go on. The founder, Brian Schechter, filled us in on why HowAboutWe is great. For what it’s worth, we did not begin our discussion by saying “welcome to TheGloss, bitch” but we thought about it.

TheGloss: HowAboutWe is all about people proposing cool dates. I hate all the things people do on dates. Please propose a date I personally would enjoy.

Brian: The most popular dates across the board – the ones enjoyed by most people – have to do with some sort of competition. So how about we go play ping pong? How about we do a game of Connect 4 at a cafe? So, those are all awesome activities to do one a date. If you want something more adventurous, how about we go to Queens to try Indian food? We get a lot of exploratory dates, like trying one of the tours that only tourists do. Or you could create a photo documentary of your walk across the Brooklyn bridge. How about we go to Night Court and then discuss the judge’s verdict? Or how about we get a dozen roses and pass them out to strangers?

TG: Those all sound like pretty okay dates. What’s your favorite date? 

B: How about we buy a pack of tarot cards and learn how to read them.

TG: What’s the weirdest date you’ve seen on the site?

B: How about we go pretend we’re married and go get marriage counseling.

TG: Coolest. Date. Ever.

B: [Deafening silence.]

TG: So, is that couple married now? 

B: We do have a lot of couples that get married. I remember the first couple that told us they got engaged off the site. Their first date was go see Shakespeare in The Parking Lot on the Lower East Side, and then for their engagement party, they had all their friends go back to Shakespeare in the parking lot to re-enact it with them. There are no dating sites where you’d celebrate that you met on a dating site, but since HowAboutWe is about real world experience it really opens it up.

TG: Are there any dates you won’t accept?

B: We have a flagging system so when people say offensive things it gets pulled out before it gets pulled in. So any “let’s fuck” dates won’t get in. And the community is active about flagging dates that are sketchy.

TG: Are you single?

B: No.

TG: Did you meet her on the site?

B: No, but we met at a HowAboutWe event.

TG: So that really worked out for you. What inspired you to start HowAboutWe? Were you looking for a relationship?

B: Aaron and I created HowAboutWe when we were in the dating world. We were both high school teachers, and we wanted to make something that was all about the actual dates people want to go on – something fun and natural.

TG: Who do you think is the typical HowAboutWe user? 

B: In talking to people about the idea over the past 2 years we’ve found it’s really a site for someone who wants to see where things go when they meet someone. It’s not for someone who thinks “marriage or nothing” and it’s definitely not a cheesy hookup site. It’s for people who want to figure out offline if someone is right for them. And we find there’s a lot of range of people who want that experience. And the people the site works for are people who want to go out on real dates and not spend a lot of time chatting online. Other dating sites can be total time sucks.

Check out all of the cool, interesting and weird dates by visiting TheGloss Dating, our new dating page, here.