Play it on first dates, subway rides with signal problems,
and everything in between.
When I was still dating in New York, I would often text the other person before the first date: “Hey, come with 3 interesting questions you want to talk about. I’ll do the same and we’ll go back & forth.”
You would think that this prompt should be unnecessary given that first dates are *all about* questions —and yet, it always made a huge difference. Thankfully, I managed to escape the New York dating vortex long ago but my love for great questions continues to this day.
In the canon of “great questions for strangers”, there is perhaps no list more famous (or wonderful) than the NYT’s 36 Questions. I was inspired to take this list and adapt it for New York City … such that people could get to know each other through the lens of the unique city they share.
You’ll find the full list at 36questions.nyc.
I also created a physical version so that one day someone could use it on a first date without staring at their phone … or pass it around at a dinner party:


What question for New Yorkers would be on your list? Reply in the comments!
And if you’re looking for even more questions to explore, my partner Marc and I also created questions-game.com several years ago.
I LOVE THESE