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Meet the guy who sets up all of Time Out’s Undateables

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Time Out New York editors

We already know many of you flip straight to the Undateables when you pick up Time Out New York every week. That's why for our first ever Reader Takeover issue we let you flip the script and ask staff writer Will Gleason—who sets up our Undateables and interviews them about how their dates went afterward—all the questions you may have about his adventures in matchmaking strangers. Readers asked, and he answered: 

RECOMMENDED: Full guide to the Reader takeover 2017

Have any of the Undateables stayed together for the long run? Any weddings to report?
Marie Assante, 34, East Harlem
Will Gleason, staff writer: I know some have had second dates, but after that they generally stop feeling the need to update me on their love lives. There haven’t been any weddings that I’m aware of, and there better not have been, considering that I’ve received no invites.

How do you explain the hearts rating system? Four hearts shouldn’t mean “Well, at minimum he didn’t murder me.” 
WG: Daters rate the dates themselves! Three stars is the average rating, and that means you had an enjoyable evening but there wasn’t a romantic connection. Four stars means you thought there might be a connection, and five stars means you think you’ll probably go on a second date.

How many people apply to be in the column?
Hannah Ongley, 30, Greenpoint
WG: Usually around 10 to 15 straight women a week, three to four gay men and two to three straight guys a week. We get only a handful of lesbians a month.

Do daters come to the office to get their photo taken? Do they not run into each other?
Mary Brownlee, 30, Clinton Hill
WG: Yes! All daters come into our office to get their pictures taken. Then I take them to the honesty couch and grill them on how the date went. I make a point to schedule their interviews at different times so they don’t run into each other, but I did have a mix-up once when they came in at the same time. There was a lot of stalling for time, running down hallways and shuffling people between conference rooms that afternoon. It was like a ’70s BBC sitcom.

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