Ask Roulette

About two weeks ago Ben and I went to Ask Roulette at Housing Works. Housing Works is one of our favorite places to go to in Manhattan. Aside from being a cool used bookstore (and thrift shop next door) that raises money for advocacy and help for people with HIV/AIDS, they host a number of really cool and fun events that we go to regularly. I’ve been to one Ask Roulette (the very first one actually) a few years ago and have always wanted to go back.

Ask Roulette

Ask Roulette

This is how Ask Roulette works. Before Ask Roulette starts, you can submit a question to ask, but if you do submit one and it gets pulled, it means that you have to answer a question. Two people sit on stage with a divider between them so they can’t see each other. Person A (left) asks his question to Person B (right). She answers. Person A leaves the stage. Person B covers her eyes and the moderator pulls out a number. Person C, whose number it is, takes Person A’s old spot. Person B uncovers her eyes when Person C is seated on the other side of the divider. Person B & C greet each other. Now Person B gets to ask her question. Person C answers. Person B leaves the stage. Person C covers his/her eyes while the moderator pulls out a new number, and so forth.

You don’t have to submit a question. You can just watch, which is what Ben and I decided to do.

Ben was pretty skeptical at first, but he really enjoyed it because many of the answers we got were surprisingly personal, introspective, and revealing. You really don’t know what you’ll get. One of the questions was, “Do you worry about your hair?” which on the face of it seems like a banal question. But the woman who received this question appeared startled, said the question was apropos for her, wondered if she should answer it deeply or superficially. The audience yelled deeply. Then she began telling us about her trichotillomania, which is the compulsive urge to pull out one’s hair. She said that this was something not many people knew about her, not even her fiance and many of her friends (surprise, fiance). She described her childhood dealing with it and how even to this day, though it’s controlled at the moment, she still worries about it and wonders all the time if her hair looks all right. We, the audience, really sympathized with her struggles. The moderator also has trichotillomania and there was a bit of a bonding moment going on there.

The other really cool answer we got was from another woman who answered a question about secrets and whether she ever successfully kept it. She told us about how she was told by her mother that her father is gay and a leg model for Sears (the latter was actually more shocking to them than the first). For many years, she and her siblings had to pretend that they didn’t know that their father was gay (who thought he was successfully keeping this away from his wife and children). The woman even received a fake Oscars for Best Supporting Actress from her mother for keeping the secret. Aside from being humorous, we really connected with her because she was being open about herself and her feelings of confusion during those years.

The best answers in Ask Roulette were not so much the funny ones, but the ones where the speakers were introspective and willing to be vulnerable with the audience. What’s surprising is just how many were willing to go there with us, strangers. I really appreciated it and at many moments was touched or moved by the speakers.

David Rees

David Rees

Another fun thing about Ask Roulette is that they bring a couple minor celebrities. One of them was David Rees, a political cartoonist and artisanal pencil sharpener. He comes off as being brusque with an acerbic wit, but there’s a deep level of caring inside him. He is very knowledgeable about many topics. He spoke intelligently (and with a biting wit) about several things. Ben really liked him (and so did I).

It was a fun evening. Tickets cost less than $9 (including the surcharge), so it’s a cheap, fun night out. I definitely recommend that you check it out if you’re in NYC. If you’re not, you can listen to the podcasts for free right here.

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