Shopping for the Perfect Shirt With Writer David Sedaris

David Sedaris is on the hunt for a specific type of shirt. “I’m old now and can’t wear anything too thin,” he explains to a store clerk. “It accentuates my man-breasts.”

Sedaris has led me to 45R, a Japanese boutique he first shopped at in Tokyo before discovering a stateside outpost here on Mercer Street in New York City. The front of the store smells like soothing incense, but toward the back there’s a statue of a naked child clutching a piece of fruit in one hand while throwing the other hand victoriously into the air. It’s just the kind of playfully bizarre decoration that Sedaris loves.

“Is your father still alive?” Sedaris asks the young clerk. Yes, the clerk says. He just turned 58.

“So he has breasts, doesn’t he?” asks the writer. The clerk nods and laughs.

When Sedaris, 61, shares intimate details of his life, he forges a bond with millions of readers and audience members, including now this clerk who busies himself finding a flattering shirt. In his early essay collections, Sedaris wrote about the homophobic speech therapy he was forced to endure as a child, his experimentation with drugs and his stint working as a Santaland elf at Macy’s. He recorded his unusual obsessions with taxidermied owls and foreign swear words. He always carries a notebook with him, and scribbles down observations that he later crafts into humorous stories. (He even tests out the notebook in various shirt pockets during our shopping trip to make sure it will fit.)

Sedaris has mined his past for eight memoirs’ worth of material, including a collection of old diary entries published last year under the title Theft by Finding. But in his newest essay collection, Calypso, out now, he looks to the present and the future. “Though there’s an industry built on telling you otherwise, there are few real joys to middle age,” the book begins. He has found some perks: he spent his 20s broke but now lives in the English countryside with his boyfriend Hugh, in a house with a guest room, the kind Sedaris fantasized about as a younger man.

The couple also recently purchased a cottage by the seaside in North Carolina and named it the Sea Section. Much of Calypso takes place in this new beach home. There, he and his siblings clash with their father over politics, and at one point Sedaris feeds a benign tumor he had removed from his body to a sea turtle—just because. But there are many downsides to growing old. Sedaris’ body is slowly deteriorating, which perhaps has led to his fanatical obsession with his Fitbit.

When Sedaris and I meet in the late morning, he has already logged almost 9,000 of the recommended 10,000 steps for the day. “If I were a lazy person, I would just walk another 1,000 steps and say I’m done,” he says. “But I’m not a lazy person.” His record is 91,000 steps in one day.

At home in England, he meets his goals by wandering through his neighborhood for hours at a time, picking up litter on the side of the road as he goes. Sedaris is the first to admit that he easily becomes consumed by routines. As a student in Chicago, he used to arrive at the same IHOP and sit in the same booth to drink the same cup of coffee at the exact same time every day. Now he has channeled his self-described obsessive-compulsive disorder into a green, if dangerous, project: as we walk alongside busy Houston Street, Sedaris spots a trash bag filled with Styrofoam tumbling into the road. He runs into oncoming traffic to grab it.

Sedaris doesn’t exaggerate his peculiarities on paper to earn a few laughs. In person, he’s the same neurotic and charming guy that his faithful readers know so well. And yet in Calypso, he occasionally drops his trademark humor in favor of meditations on regret and mortality.

Sedaris has previously written about his mother in reverent tones: her six children vied for her attention, and she held court at the dinner table every night. She even coached a young Sedaris on how to tweak his anecdotes to make them funnier. But in the considered and brutally honest Calypso essay “Why Aren’t You Laughing?,” Sedaris admits that he regrets that he never confronted his mother about her alcoholism.

In an essay titled “The Spirit World,” Sedaris remembers his last interaction with his sister Tiffany before she died by suicide. The two had a difficult relationship and had not spoken for four years when she appeared unannounced at one of his readings in Boston. She called to him from the stage door to the theater. Sedaris ignored her, turned to a nearby security guard and asked him to shut the door. He never saw her again.

“I feel the audience giving me the appropriate reaction when I talk about shutting the door in her face,” says Sedaris of reading that essay aloud on his book tour. “They didn’t expect that, and then they have to recalibrate their feeling toward me. When I read that the first time, I thought, Do I really want to admit this? But it seemed false not to. If you try to make yourself look better than you are, that’s bad. Especially if you’re making other people look bad, you have to be up-front about how bad you are.”

Sedaris says he doesn’t regret anything he’s ever written. But he does dislike his early work. Back then, he didn’t have the luxury of reading stories aloud in front of an audience dozens of times and then tweaking the language before publication. “Everything in my first four or five books I would completely rewrite,” he says. “I sign those books sometimes, and I think, Whatever is in here cannot be good.”

Sedaris’ performances are essential to his craft. During his years at the Art Institute of Chicago, he reveled in the laughs he would get from his fellow students during workshops. These days, he reads essays aloud on tour, marks down the audience’s reactions to certain sentences, returns to his hotel room to revise the story and then adjusts the delivery the next night. He read each of the essays in Calypso onstage at least 50 times before the book was published. He loves performing for an audience and even schedules tours when he doesn’t have a new book to promote.

He also taps his audiences for material, chatting with every reader who stands in the book-signing line. A week before we spoke, a woman in Calgary, Alberta, claimed that her boyfriend was planning to get a tattoo of a corn dog on his face, which might make for a good anecdote in an essay if Sedaris could confirm it was true.

A doctor he met at a reading in El Paso, Texas, volunteered to remove that benign tumor he later fed to a turtle. Sedaris happily took her up on the offer, and in the wee hours of the morning he drove with her to a clinic for the surgery. He never goes to Apple’s Genius Bar anymore; he simply asks from the stage whether any attendees can fix a MacBook and offers them a chance to skip the line in exchange for tech support.

That’s no small offer. The longest Sedaris book signing lasted over 10 hours. As we stroll through Manhattan, he shows off the Band-Aids covering his arms. He was signing books for so long the night before that his elbows began to bleed through his shirt. “Maybe that’s what I need,” he says. “A fatty shirt that also has elbow pads.” He looks at me. “Do you think they carry that?”

Quick questions for David Sedaris:

Have you ever tricked your Fitbit?

Sometimes my friend Dawn will wake up before me, take my Fitbit and get in my steps. I go so far over the recommended amount most days that I think it’s O.K.

Why do you hate having your picture taken?

So many photographers went to the Annie Leibovitz school of photography and think if you’re not being humiliated physically, then you’re not revealing your true self. I’ve been asked to stuff things in my mouth and get into a swimming pool with my clothes on.