Illustration by Stavros Damos
Illustration: Stavros Damos

I was a kid raised with great expectations. My parents and everyone said, “You’re so bright. You’re going to do so well.” So early on, I acquired impostor syndrome: “Am I really this good?” I was not at ease socially—still am not, really—but I was also desperate to be accepted, so I ended up a theater kid because it’s a way to be in front of people with instructions.

I became the host of Wait Wait … Don’t Tell Me! on the first week of May in 1998. If I hadn’t gotten that phone call, I probably would have ended up in L.A. writing legal dramas for TV.

There’s an expression: “You either laugh or you cry, so you might as well laugh.” My marriage failed spectacularly, like the Death Star explosion—the digitized remake where Lucas went back and made it even bigger. My kids wanted nothing to do with me for reasons I can’t even begin to explain. And I was completely ready to curl up in a ball in the corner and starve to death and never move until all was over. But I have this job, and my job is being funny. I have discovered that you cannot do my job in a bad mood, because people can tell. And I found that being forced to be funny made me feel better.

Not only do I need to be busy, I need intensity and a deadline. I’m one of those people who need adrenaline.

The great thing about public radio fame is you get to turn it on or off. When I go out onstage, everybody goes, “Yay!” But I walk down the street, and nobody knows who the hell I am.

When we do the show, anybody who wants to come say hello can come say hello. They line up 40 feet deep. And I take it very seriously. I want people to walk away feeling good about the fact that they’ve entrusted me with their time. But every week it’s a struggle for me. Because I get tired of talking. I just want to sit and have a martini and be quiet.

There’s no part of your life where there’s no input, so running is a very good way to get away from that. People say, “Oh, I can’t spend that much time in my head.” No, you should! And running is a natural antidepressant. I needed the artificial ones as well.

I never refer to myself as a survivor of the Boston Marathon bombing. I never even call myself a witness. I was there. It was the first time I guided a blind runner. We had just finished. And then five minutes later, the bomb went off.

If you have a bit of celebrity and you don’t use it for somebody’s benefit, then you don’t deserve to have it.

I had dinner with three porn stars in 2005. One of them was Stormy Daniels. She was hilarious and smart as a whip and could tell a story like nobody’s business. She was the total porn star—diaphanous dress, heels, the whole deal. Let me put it this way: I remember her quite vividly.

Some people are just born to be alcoholics. They have that first drink, and there you are. And that, of course, leads them into a dark place. Sometimes I feel that way about Twitter.

When I was training for the 2010 Chicago Triathlon, on a Wednesday morning in La Grange Park, I got whacked by an orange Nissan Versa and managed to snap two transverse processes on my lower vertebrae. Apparently—and this is kind of fun—I reflexively threw my body in front of my bicycle to protect it. So I spent four days in the hospital, but the bike was fine. My helmet, which cracked all the way through on the back, hangs in my office to this day as a reminder to always wear my goddamn helmet.

The people you love are the kind people, the ones who treat you with delight when they see you. These days, instead of struggling to be the most amazing, leave-my-name-in-the-sands-of-time person, I’m trying to be that guy.