Ask Roulette is the conversation series (and one-time podcast) where strangers ask each other questions live on stage. It's a combination of storytelling, improv, and game show. I host it with the incredibly talented Eli Bolin as house band.

Come with a question you want to ask a stranger, silly or serious, and see what happens.

Here's how it works: As you arrive, you submit a question you want to ask a stranger. It could be anyone in the room. You don’t know who you’ll be asking your question to. That’s the magic of Ask Roulette.

We have an every-other-month residency at Caveat NYC. Here are our upcoming dates:

Thursday, 12/28/2023 7:00pm - TICKETS AVAILABLE
Thursday 2/22/2024 7:00pm
Thursday 4/25/2024 7:00pm - TICKETS AVAILABLE
Thursday 6/27/2024 7:00pm - TICKETS AVAILABLE
Thursday 8/22/2024 7:00pm
Thursday 10/24/2024 7:00pm

Through 2016, we had regular shows at Housing Works bookstore in Manhattan. We've also performed in Washington, DC, on WFMU radio, and elsewhere.

 

Questions are serious or silly, and answers are short or long. Over the course of the evening, you'll get unexpected and honest connections, surprising anecdotes, and honest conversation. You'll be sure to laugh too. 

Previous special guests have included

  • Roy Wood, Jr.

  • Heben Nigatu

  • W Kamau Bell

  • Chris Gethard

  • Pablo Torre

  • Awkwafina

  • Jad Abumrad

  • Julie Klausner

  • Kurt Braunohler

  • Desus Nice

  • Baratunde Thurston

Some of our favorite questions

  • How do you get your hair to do that?

  • What’s the best compliment you’ve ever received?

  • If you could bring back and historical figure for a 15 minute conversation, who would it be?

  • Is there anything that is too serious to joke about?

  • If you could shoot any condiment from your belly button, what would it be?

  • Is America the greatest country on earth?