17 NYC Conversation Starters That Won’t Make Things Painfully Awkward

Katherine Ripley Katherine Ripley

17 NYC Conversation Starters That Won’t Make Things Painfully Awkward


We’ve all been there: you really want to land that cute guy or gal you see every week in the coffee shop, but you just can’t think of a way to strike up an interesting conversation. Before you resign yourself to a life of staying in every night and binging on Netflix and Ben & Jerry’s, let us give you some suggestions. Here are 17 ways to start a conversation with a cute New Yorker:


1. If you could make a new law for New York City, what would it be?

2. What’s the best season to enjoy New York?

3. How many freelance jobs do you have?

4. Would you rather be a traffic director or a skyscraper window washer?

5. What woman would you make into a Central Park statue?

6. Would you rather live on a houseboat in the East River, or on the very top of the Empire State Building?

7. Would you rather keep a pigeon or a squirrel as a pet?

[Zoli Juhasz]
[Zoli Juhasz/Flickr]
8. Where’s your go-to pizza place?

9. Where’s your go-to deli?

10. Would you rather live 15 blocks from a subway stop or live in the middle of Times Square?

11. Weirdest street performer you’ve ever seen?

12. New York Times or Wall Street Journal?

13. Favorite Broadway play?

14. Favorite place to read?

[Roman Kruglov]
[Roman Kruglov]
15. If you could build a zipline anywhere in the city where would you put it?

16. If you couldn’t live in New York anymore, where would you live?

17. Which NYC landmark would you say best describes yourself?

Pro tip for guys: don’t try to answer that last one with any skyscraper. It’s not going to work.

For more dating advice, click here!


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