Editor’s Note: Yes, and then No | September 2025

I showed up for my first improv class at 6pm on the dot. Not early—because that might involve small talk or standing awkwardly in a half-empty room. Not late—because I’m not rude. (Lateness is a form of narcissistic personality disorder, an unconscious assertion of status, importance, or special rules. Beware the chronically tardy.) Punctuality is how I keep the chaos of life at bay. Board meetings, dinner with friends, dentist appointments—I like to arrive exactly when things are meant to begin.

The class was held in a nondescript community arts center. Two rows of chairs had been set up. There might well have been an Al-Anon meeting in the time slot before us. I took a seat between a woman in her 70s and a woman in her 30s and made no effort to speak to either of them.

Our instructor, Sam, introduced herself and laid out the basic ground rules: no politics, no profanity, no sexual innuendo. Basically, no fun. She gave a bit of background about her own improv journey, then got us all on our feet in a circle—holding hands. I stood there, vibrating with the energy of a man doing something very stupid on purpose.

We went around the room and said why we were there. The 30-something next to me—Jen—looked terrified and said as much. She worked in PR and wanted to challenge herself. The older woman on my other side said she’d acted in her younger years and was trying to rediscover that part of herself.

When it was my turn, I said I was a magazine editor and spent most of my day telling people no, sending out polite but firm emails that boil down to “thanks but no thanks.” I wanted to try saying “yes, and” for once.

Circle of Awkward Energy

That first level of improv class—Level 1—was four three-hour sessions. That’s it. But within those 12 hours, Sam laid out the ethos of improv: Say yes, strive to make your scene partner a star, trust the moment, and let go of control. Don’t try to be funny—try to be present. The laughs come when people commit to the absurdity with sincerity. Improv isn’t about performing a script. It’s about discovering one in real time, together, by listening deeply and responding honestly. It’s less like writing a play and more like walking into the woods without a map and agreeing no one’s to blame when you get lost. (Which is crazy to me—someone is always to blame.)

I wasn’t sure what to make of it. Was I really the kind of person who does improv? Who flaps his arms and shouts gibberish in a circle with strangers on a Monday night? I looked around the room, trying to figure out if these were my people or if I’d accidentally joined a cult that worshipped the god of Awkward Energy. Part of me thought, maybe this is my tribe. Another part thought, maybe my tribe is at home on the couch watching “The Bear.”

After Level 1 was over I had to decide: Go deeper or walk away. I wasn’t sure I liked improv or that it liked me. But I chose to move on to Level 2. Because I’d made a deal with myself: I was going to perform in front of an audience. I give speeches pretty regularly, and I’m comfortable holding space in front of a room—but never without a script. I wanted to know what it would feel like to go up there empty-handed, armed with nothing but panic and a wry smile.

Level 2 was four more sessions, building toward a live show. Most of the time was spent learning new games. The other bit was technical: how to stand, how to enter and exit, how to not completely tank the scene for your partner. There was a bit of a summer camp vibe: We were in it together, sweaty and trying, and looking to one another for cues on what was working, and the esprit de corp of our fledgling troupe.

My classmates were a delightfully improbable group. Howie, a bald man in his 40s with great comic timing. Don, a Gen X Google employee who invited everyone to the crossword construction night he hosted at a local bar. His wife, Elizabeth, a geologist from England with an air of quiet erudition. Karen, a sharp and funny lawyer. Rob, a mulleted musician in a Hawaiian shirt. Cindy, a retired high school Spanish teacher with kind eyes. James, a tall, Jersey-born 20-something with the golden retriever energy of a handsome man who’s never had to do much thinking. Dave, a DMV investigator who told me he carries a gun. Thomas, a mini Kenny Loggins lookalike. And me.

We played games that made no sense—passing invisible balls, tossing made-up noises around the circle, stomping and yelling nonsense in unison. I didn’t understand what we were doing most of the time, but I went along with it. There was something freeing about it. Maybe even useful. I began to notice when my body tensed before a scene, when I reached for a clever line instead of a true one, when I backed away from vulnerability in favor of control.

Then the day of the performance arrived.

That morning, Lee Anne was working at the Habitat for Humanity ReStore, where she’s the manager. John Scurti—“Rescue Me,”“The Marvelous Mrs. Maisel”—stopped by, as he does from time to time. He’s friendly with Lee Anne. When she told him I was doing improv that night and feeling nervous, he said, “There’s nothing to worry about. An actor’s greatest fear is forgetting their lines. That’s not an issue in improv.”

And he was right. Technically.

Dreaming in French

I was cast in two scenes: Slide Show and Sing It!

I should say, in my defense—or maybe in confession—that cheating isn’t exactly new to me. I’ve cheated at many things in my life: card games, Monopoly (be the banker, obviously), countless tests. I was good at cheating. I had systems. Peripheral vision like a hawk. Strategic seat choices. Whispered signals. But I didn’t cheat because I was lazy (well, not only because I was lazy). I cheated because of how I was raised.

I went to Catholic school, where high marks weren’t just rewarded—they were demanded. There was no talk of process or effort or “learning.” You either got the grade or you didn’t. This wasn’t Montessori finger painting. This was: Write the correct answer in the correct box or disappoint God, your parents, and the ghost of every nun who ever taught long division.

I stood there, vibrating with the energy of a man doing something very stupid on purpose.

In my freshman year of high school, I was placed in the honors track. A mistake, it turned out. My ability to cheat on standardized tests far outpaced my ability to do actual academic work. I suddenly found myself among the brightest kids in the school—the ones who would go on to be valedictorians, Ivy Leaguers, TED Talkers. And they all cheated. Constantly. Casually. Elegantly. They passed answers during tests with coded eye movements. They kept textbooks open in partially unzipped book bags. They developed little systems and mnemonic triggers and fingertip tap codes to get from a 97 to a 100. They weren’t salvaging failure. They were polishing perfection.

And I’m convinced the teachers knew but they looked the other way. These were their stars. Their track record. Their college placement stats. These were kids who were going places. What was a little tactical dishonesty between champions?

This was the moral weather I grew up in. This was the playbook I brought with me into improv.

So when I wrote a song before the performance—a song called “Dreaming in French,” about a horny neighbor crushing on the new topless French emigre on his block—and then carefully steered the scene to set up a cue for that exact song, I wasn’t breaking a rule. I was following an old instinct.

The game was called Sing It! One of us asked the audience for a manual labor job (someone shouted, “boxing items on an assembly line”). The four of us began miming conveyor belt drudgery. Sam, offstage, would ring a bell when she heard a line that seemed like it wanted to be a song. That was the premise.

So I said, “Hey, did I tell you guys I’ve been studying French?”

Sam rang the bell instantly, just like I hoped she would. I stepped forward, shuffled my feet, and snapped my fingers like the washed-up lounge singer I would never be, and sang “Dreaming in French”:

I got this neighbor Brigitte

she just moved onto my street

Brigitte is topless a lot

man she’s really so hot

tres chaud—that’s French—for hot

And now I’m dreaming in French

Brigitte has got me dreaming in French

I don’t know how long this dream will last

but I’m dreaming in French.

Français, mais oui.

It landed. Got laughs. Got applause. People told me afterward how brave I was. But it wasn’t bravery. It wasn’t even improv. It was muscle memory: anticipate, control, avoid risk. Make it look spontaneous but know the ending before you begin. It was a habit born in a classroom where failure meant shame and success meant safety—no matter how you got there.

And I walked offstage feeling…relieved.

I hadn’t failed. I’d nailed it. As has always been expected of me.

Cheat to win. Still works.

Exit, Pursued by Panic

Some people run a marathon and fall in love with distance running. Others cross the finish line, thank their knees, and never sign up again. I’m the second kind. I did the work. I showed up for every class. I tried. I failed a little. I performed in front of friends and strangers. And I stepped offstage with a better understanding of how much I crave control—and how deeply weird it feels to let go of it.

I couldn’t have done it without the troupe. Truly. They had my back from the first awkward circle to the final blackout. We were a ragtag bunch—lawyers, geologists, coders, musicians, DMV agents, dreamers—and we were all, unmistakably, beginners. Baby swimmers tossed into the deep end. And yet, no one sank. We splashed, flailed, floated, and cheered for one another like it mattered—because it did. Every goofy premise, every cracked punchline, every scene that nosedived, and somehow stuck the landing: we made those moments together. Their support never wavered. They would have done anything to help me succeed—and they did. That’s the thing I’ll miss the most. Not the games. Not the laughs. The feeling of being buoyed by others.

Improv, at its best, asks you to trust. Trust your partner. Trust the moment. Trust that you can build something out of thin air. That’s not my comfort zone. I’m not sure it ever will be. But I glimpsed it. And that might be enough.

If nothing else, it reminded me what it feels like to be bad at something. To start from zero. To do something awkward and unpolished and real. And to do it in community.

Yes, and—I’m out.  

This article appears in September 2025.