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An eye for a toe, and other quandaries for potentially terrible people

Wes Hazard

Boston’s Wes Hazard is a lot of things — standup comedian, storyteller, poet with an MFA in creative writing. Since the release last fall of “Questions for Terrible People: 250 Questions You’ll Be Ashamed to Answer,” he can add author to that list.

The concept: Pose comedic questions that might just reveal a person’s inner awfulness. Would you rather be cremated and your ashes baked into cookies served to your enemies, or have your body preserved and posed in a sports venue? Would you be willing to lose your pinky toe to save a friend’s eye?

We decided to ask Hazard some questions of our own.

Q. How many terrible people do you know that you had this many questions for them?

A. I think when people think about “terrible” they think, you know, like classic dictator evil. But the nature of this book, people are terrible in thousands of small ways each day. They’re so small you can get away with it. I’ve found very few people in my life who aren’t occasionally terrible.


Q. And these questions are your way of finding out how terrible someone is?

A. Exactly. The book works almost like a game. You can certainly sit and read it yourself and have some laughs, but it’s really good for long car rides or ice breaking, getting to know people. It’s really fun to find out with your friends which kind of terrible you are.

Q. Is this something you’ve done for a while?

A. No, no. But what I have done is, since the book came out, I’ve been taking it to some of my live shows and I’ll just have a section where I take 10 or 15 minutes and either read questions aloud or show them on slides on a projector and just ask the crowd the questions. You’ll have a couple, or a small family group will be together, and you’ll ask a question, and usually it’ll be a binary one, A-B, which of these options would you choose? And you’ll see one person say one thing and the other people in their party say completely the opposite. And then there’s almost disbelief when they go back and forth amongst themselves, because they can’t believe that someone would pick something so opposite to them.


Q. Did any of these questions come from a real situation? Did you ever find a dead body with cash on it?

A. No, I have not been . . . I was about to say, “I have not been that fortunate.” I don’t think I’d call that “fortunate.” But most of them are sort of just hypotheticals.

Q. What was the inspiration for these?

A. It kind of came out of nowhere. Someone who I had taken a poetry writing workshop with and had not spoken to in almost five years was at my publisher, Adams Media, and reached out to me and said, “Hi, we have an idea for a project — we’re sort of thinking of it somewhat like ‘Cards Against Humanity’ in book form. We need someone funny to write it.”

Q. Did it put you in a strange mind-set to be brainstorming these things constantly?

A. Absolutely. Obviously, I was tasked with writing questions for terrible people. Everybody’s going to have their own interpretation of exactly what that means. I really only ran questions by — aside from my editor — just my best friend Dave. He would just bury his head in his hands and be like, “Why? How?” And that’s when I knew things were going well, when I got that reaction.


Q. They do run from sort of cutesy to more violent and transgressive.

A. There’s a fairly wide range. The worst of the worst is, I would still say, PG-13 or on the line, possibly up to R. Some I would absolutely break out at a family reunion, expect all the different generations to have a ball, and some I would never, never, never discuss in front of an older uncle or a grandparent or something like that.

Q. Have you ever asked one of these questions to someone and gotten an answer that made you wish you hadn’t asked?

A. I can’t say that I have. I have gotten quite a few people taking questions much more deeply than I imagined. I have a question along the lines of, “You can wake up every single day of your life and find $100 under your pillow, [and] if you do so, everybody currently living on the planet will die one day earlier.” Essentially you’re selectively eliminating 7 billion days of life off the planet. I asked that to a crowd and I was rather surprised at the answers. The debate that broke out — it was very philosophical. I was surprised by that, about where they took it, what I thought was just sort of a fluff comedy question, and people really took it to heart and spent a long time talking about it. I was very happy about that.


Wes Hazard

Pavement Comedy Night with Dylan Krasinski, Michael Bain, Molly Dugan, Isaac Ruben, and Will Smalley. Feb. 17, 6:30 p.m. At Pavement Coffeehouse, 736 Commonwealth Ave., Boston. Tickets: $5, 617-277-8737,

Interview was edited and condensed. Nick A. Zaino III can be reached at