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

You’ve got to propose a good date. Part of what our users really like about HowAboutWe is that you can actually tell a huge amount about a person based on the dates they propose. The dates that get the most responses seem to be ones that have a bit of personality—they’re not crazy over-the-top but they’re not vanilla. You need to take the risk of saying what you really want to do.

You also need to be game for going out. People on our site are not there for endless chat relationships. That’s precisely why a lot of them are leaving the other dating sites—they’re tired of weeks of bullshit online conversations before an awkward interview-ish date. They just want to exchange a few messages, go out, and see what happens. There’s a kind of fun, an openness, at the heart of HowAboutWe.

What’s the biggest mistake men make when proposing dates or while on dates?

When proposing a date, there are a few pitfalls:

First, grammar. You’ve got no idea how many girls tell us that spelling mistakes, misuse of punctuation, and even shitty syntax are deal breakers. The correct use of a semicolon is like a victory ticket.

Second, unoriginality. Again, it’s not that girls are looking for some insane costume-dress-up-scavenger-hunt-on-a-motorcycle-diamond-stealing extravaganza (although that sounds kinda hot). But "How about we...get a drink" is just boring. Step it up. Name the bar and the drinks: "How about we...drink American Trilogies at White Star." Much better. It’s not that the dates need to be long and involved; a quick classic date is a winner. Class is key.

When on the date, character is the thing. There’s nothing cute about narcissism, and a date is not an interview about YOU. Not listening is a huge mistake. A female friend said the other day, "The best drink on a first date: Grey Goose and soda, with a lemon. And yet there are so many guys that come back with a lime instead." Not making eye contact means you are elsewhere—and elsewhere is unattractive. And it’s about fun—a guy who authentically creates a sense of playfulness and makes it infectious is a skillful dater.

By "infectious," I take it you’re referring to syphilis. What are some of your favorite date activities in NYC?

Dumplings and Jameson at Bar 169 on the Lower East Side is a favorite. Seeing new shows—like the recent Marina Abromovic exhibit at MoMA—is always a win; you can tell so much about someone by how they engage with art...and even if the date is sparkless, you saw the show. Bars with fun side-projects (jukebox, noteworthy drinks, bocce)—these are solid. An outer-borough trip to a touted eatery can be good, like Sripraphai in Queens or the Indian spots in Jackson Heights. Pool hopping.

Are you getting sick of friends asking you, "How about we [fill in the blank]"?

Nah. Our friends have been amazing throughout this whole process, offering to help in countless ways—sharing the site with their friends and offering lots of moral support. We joke about HowAboutWe dates all the time. It’s not uncommon to get a few text messages in a day from friends who have come up with new over-the-top HowAboutWe date ideas.