Get us in your inbox

skyline bridge
Photograph: Shutterstock

20 New York City conversation starters

By Dana Varinsky

Living in New York means we deal with strangers all the time—on the subway, squeezed too close at the table next to you, at your friend's friend's birthday know what we're talking about. For the most part, that's what keeps the city interesting and unpredictable. But sometimes, when you realize you've lost your friends at the bar and have to strike up a conversation with the random dude standing next to you, a little conversation prompt can't hurt. A new app called Blush no More, which generates ice breaker questions to ask at parties and reunions, is designed to alleviate that problem. But NYC life demands a very specific set of queries, so we figured we'd come up with our own. Next time you're trapped at an uncomfortable networking event, give one of these a try. 

"Would you rather have a dishwasher or a washer/dryer?" 

"Which is more awkward: Hearing your neighbors fighting or having sex?"

"What’s your go-to Seamless order?"

"Favorite subway line—go!"

"Dunkin' Donuts: into it or against it?"

"What do you think is the best pizza in NYC?"

"What's the craziest thing you've seen—or smelled—on the subway?"

"What’s your favorite public place to cry, scream or otherwise lose composure?"

"Okay, ask me five questions and then guess which neighborhood I live in based on my answers."

"What’s your current dietary restriction?"

"If money wasn't a concern, which neighborhood would you live in?"

"What's your opinion on Woody Allen?"

"What’s your record walking time from front door to train station?"

"How many roommates do you have?"

"What’s your favorite walking music right now?"

"Would you rather live 15 blocks from a subway stop, or in the heart of Times Square?"

"So, where did you move here from?"

"If you had to leave the city tomorrow and got to eat one last meal, which restaurant would you go to?"

"New York—great city or the greatest city?" (Thanks for that one, Colbert)

And, of course, the classic: "So how much rent do you pay?"


    Popular on Time Out

      Latest news

        Read next