Sitting in a Main Street coffee shop, an empty espresso cup and her laptop in front of her and a New Yorker tote bag at her side, Bryn Durgin is reconstructing a vivid memory from her childhood. It’s about her father, who was “prone to disaster” – falling into the pool annually while trying to take off the cover; losing a front tooth to a swinging carabiner as he tried to take down the volleyball net, suffering more than his share of concussions and injuries from one mishap or another.

In this case, the family – Durgin, her parents and her two brothers – were on summer vacation, enjoying a trip to a water park from their rural home in northern New York near the U.S./Canada border, an area so remote it was a two-hour drive to the nearest mall. Her father flipped while riding in an inner tube, spitting him into the pool where he hit his head on the bottom and suffered another concussion.

The family waited anxiously for hours as he was tended to behind the scenes. The rest of the park visitors began to leave. The sun started going down. Finally, they saw a familiar figure in the distance, assisted by park personnel, walking unsteadily toward them.

“I remember my Dad being returned to us,” Durgin recalls, grinning again even now, decades later. “The park is empty, he’s in soggy swim shorts, but he’s covered in all this swag they’d given him. That vision of him, as a kid, I thought was so funny. But of course, what happened was not funny at all.”

Durgin, the director of programming at Sarasota’s Bookstore1 and a frequent contributor to The New Yorker, learned early on that humor isn’t just about a punch line. For her, it’s a philosophical filter for viewing the world, with all its adversities, ironies and yes, even tragedies.

“Humor is how I metabolize fear and grief,” she says. “Often what I’m most attracted to, I don’t know whether to laugh or cry. Things are so out of our control, almost everything, and there’s something funny about that, the things happening to us constantly. A lot of humor is about the systems we build to steady ourselves, to brace ourselves for loss, to live with uncertainty.”

It’s a perspective she will share in “The Mechanics of Funny,” a workshop she’s leading at Bookstore1 on June 7, a perspective, that continues to color not only her writing, but her approach to life.

In the beginning

By her own admission, Durgin’s childhood was “Norman Rockwellian.” Her grandmother sewed her dresses. Her father taught English and drama and coached football at the local high school. Her mother taught special education and later became a school principal.

“Both of them had a really good sense of humor,” she recalls. “My Dad specifically was know for playing pranks and he was absolutely hilarious, so, so funny. I peed my pants laughing with him many a time. Sometimes he was funny without even knowing it.”

As teachers, both parents had the summers off, and the family would drive cross-country in a camper to the western states, Eric Clapton songs playing “endlessly” on a CD. For each trip, Durgin was given a journal to document whatever she chose.

“My journal would turn into skewering my brothers and making fun of them,” she says. “But I guess that’s kind of how I started writing.”

She was already a voracious reader who “devoured books.” Her brothers still make fun of the soundtrack of their childhood – their sister gently rubbing the edge of a book’s page as she read. The first book she fell in love with was poems by Shel Silverstein, which she now sees as “a perfect example of good humor for a child.”

“I was always into writing,” says Durgin, who entered a few poetry and essay contests in her youth, but never had much interest in being published. “I just write to think; it isn’t necessarily writing for other people to read. If I can’t write something down, it’s like I can’t understand it.”

Yet there’s a telling entry in one of her early childhood journals in which she asks herself, “What do you want to be when you grow up?”

“What I would like to be when I grow up is a writer,” she wrote. The entry continues on, painting an idyllic life involving living by a lake with two dogs and two cats in a “butiful” home with friends and family nearby and writing stories “about peaceful things and some-times poetry.”

The next chapter

Some of that has actually materialized, though not exactly in the way Durgin originally envisioned. She is a writer, she does live near water (the Gulf) and she tries to catch the sunset most nights. But home is a tiny apartment, overflowing with books, art and emotional artifacts and the “butiful” place where she is surrounded by friends, is the bookstore. At the moment – and for the first time in her adult life – she is without a pet, having lost her dog, Lil’ Buddy, last December after almost 19 years.

But back then, Sarasota wasn’t even close to being on her radar. After years as an excellent, motivated student, in 11^th grade she got mononucleosis and temporarily lost all drive and interest in school.

“I became insufferable,” she recalls. “I was like, ‘None of this matters, who cares, I’m not going to class. I’m just going to focus on the people I care about.”

What she was sure of was that, after graduation, she wanted to escape the remoteness of her childhood home. Since New York City was her target destination, her high school counselor encouraged her to apply to St. John’s – at least Durgin thought she was applying to St. John’s University in Queens, New York. In fact, the application was to St. Johns Fisher University in Rochester, an exclusive and expensive private Catholic school, originally for boys, where she was offered a generous scholarship.

She accepted and embraced the opportunity as “a fresh start, a clean slate,” achieving a 4.0 grade average every semester, majoring in journalism and minoring in peace and social justice studies. An intense and serious student who “cared about a lot of dark subjects,” she spent time studying abroad in Italy and South Africa, where she became certified as a community development worker.

“It was a way to combine goodness, doing something I could feel good about, while also writing,” Durgin says.

However, the intensity and mystique of New York City still lured and even before she graduated in 2011, she’d secured a position as a dog walker in Manhattan, which she hoped would be a good way to familiarize herself with her new environment.  She shared an apartment with five actors; her “bedroom” was a hallway, where you had to climb on top of the bed in order to open the French doors.

Perhaps the first test of her capacity for finding humor in disaster came the day she moved in when she went out with her roommates to celebrate her big move and returned to find the apartment had been burglarized. All electronic and digital devices were gone, including the laptop with all her writing. Without a cell phone or Google maps, she was left to navigate the city with her four-legged charges unaided.

After applying to and receiving offers for a number of other positions, she accepted a second job writing copy for an advertising magazine with offices in Herald Square.

“I was like, Herald Square! NEW YORK! I have made it!” Durgin says, laughing, of what turned out to be a slog, churning out gossipy blurbs from a windowless office. “It was a content farm.”

She subsequently applied three times for writing jobs with a start-up bakery in Soho that was producing tiny, handcrafted cupcakes based on the idea that people should be able to eat a sweet treat without a heavy commitment or a guilt trip. On her third interview, she met the bakery’s founder, Melissa Ben-Ishay, and they hit it off. Which is how she came to be the Director of Learning & Development for Baked by Melissa, now nationally known not only for its signature cupcakes, but for the founder’s massive internet fame as a lifestyle influencer and cookbook author.

Durgin, along with a cohort of 20-something colleagues, took on her new duties with alacrity and enthusiasm, even while acknowledging it was far from writing nirvana.

“I threw myself into it 100 percent,” she says, “but it was also copywriting. So I kept writing short stories for myself, always doing exercises. I would meet another person who was writing and we’d share. I was always writing, but never submitting my work.”

A detour for family… and love

At the same time, she was growing increasingly aware of wanting to spend more time with her father, who had been diagnosed with early onset Alzheimer’s when she was a teenager. Her mother, who was considerably younger than her father, was still working full time. For a time Durgin took family leave from her job, then left the company completely to work on a film project in Singapore, followed by writing a children’s musical with her first writing partner.

However, in 2017 Durgin moved back to northern New York — to the house next door to her childhood home — to care for her father full-time until her mother could retire. In 2020, after her parents moved to Bradenton, she followed them to Florida to continue helping with her father’s care.

“I did not MOVE,” Durgin says. “I came down here thinking I would be here temporarily, I was always was going back to New York.”

A year of caregiving turned into two, and then three. As her father’s illness progressed to the point where he asked her multiple times to marry him – a connundrum she’s shared, with humor and painful poignancy, as a featured storyteller for The Moth’s Mainstage – Durgin found herself “hyper-perceptive, almost unbearably present.”

“I tried to make every little moment as wonderful as it could be for him and it made me very thoughtful,” she says. “All those tiny things that make up your life, all the things he loved, made me aware of all the things I love and you want them all the time. It’s made me gluttonous, but not in a bad way.”

Then, completely out of the blue and unexpectedly, she fell deeply in love. It seemed more good fortune than she could imagine and she thought, “Wow, I can have that love and my Dad too.” When a parttime job working for Bookstore1 materialized – a job that gave her access to the books and writers she’d always loved – she accepted that her relocation was meant to be more permanent.

But as Durgin’s writing will often remind you, life isn’t quite that predictable. Her magnificent romance began to unravel, ending definitively on a Zoom call. A month or so later, her father died. Reeling from the devastation of both losses, she clung to the “family” she’d found at Bookstore1; it hardly seemed the time to uproot herself again.

“I was so inside out, just raw,” she says, “and I felt really embraced by the bookstore and just so deeply supported. Once you’ve had that kind of bonding experience, it changes things in a magical way. These were people who knew me before my Dad died. And now they know me after. They’d seen that evolution.”

A month after the loss of her father, the bookstore moved to its current spacious location, on South Pineapple Avenue in Sarasota and Bryn moved into a position as its director of programming, leading events and workshops, including the store’s popular Banned Book Club. Her desire to write, which had understandably fallen by the wayside during her father’s decline, now began to resurface.

“With my Dad, my focus was 100 percent on him,” she recalls. “At that time I didn’t care about sending a piece to a publication. My every thought was revolving around his caregiving. Now that was gone, I could shift my focus and exist in another way that I hadn’t for so long.”

After a trying year, a year to try

Durgin committed to making 2022 her “try” year.  She started writing again and began submitting her work to publications. One of the first was The New Yorker, perhaps not the most logical choice for a largely unpublished young writer trying to get a foot in the door. But she didn’t hesitate.

“My thought was just, ‘Why not start at the top?’” Durgin says. “Why not? Just try. After all, it was my ‘try’ year.”

The first piece she submitted was meant for the magazine’s Shouts and Murmurs humor section, sparked by thinking about books that were in the midst of being banned by Florida schools. She wrote in the voice of a person submitting an insistent letter to a superintendent or board of education about getting these books, many of which she’d read and admired as a child, off school bookshelves.

The piece, which still hasn’t been published, was rejected. But the editor’s note she received was all the encouragement she needed: “Sorry to say, I’m passing on this one, but it had some great moments. Please send me more.”

So Durgin did, immediately. And her next submission, “What To Expect When You’re Expecting To Publish Your First Book,” was accepted. The piece hilariously compares the anxiety, physical changes, and lifestyle adjustments of preparing to release a book to the experience of pregnancy. (Not that Durgin would know; she’s never been married and has no children.)

“To see your name in The New Yorker font even, it was just so intoxicating,” she remembers. “I felt giddy, just so happy and thankful and all of those things. To have my work in the thing I love reading most. It felt so good to be part of something I’d so long admired. I’ve carried a New Yorker tote bag forever.”

Since then the magazine has published Durgin’s work regularly, some for the magazine’s culture desk, but mostly humor, including  “Your Slow and Sad Descent into Bird-Watching,” a satirical, self-deprecating essay tracing a reluctant transformation from a casual observer to an obsessive bird-watcher; “Choose Your Own Adventure: Starting a Garden,” a branching narrative about urban gardening, framing the gardener as a helpless victim to nature and her own performative pursuits; and a cultural commentary, “One Woman’s History of Unpaid Labor in Romantic Relationships,” written in the form of a resume reframing the challenges of dating as corporate job titles and professional responsibilities.

She’s also been published in Slackjaw (“Pools You Should Never, Ever Swim In,” (the “pools” including dating pools, talent pools and gene pools) and the Los Angeles Times,“What Do ‘Dog Years’ Measure?,” an illustrated comic, with Navied Mahdavian, about her longtime pet, Buddy, that is at once funny and heart-wrenching).

In 2024, she was accepted to and attended the St. Nell’s Humor Writing Residency in Williamsport, Pennsylvania, founded by Emily Flake, a humor writer and staff cartoonist for The New Yorker and named for Nell Gwyn, a comedic actress and madam who was the toast of Restoration England. The residency not only served as a further catalyst for her humor writing and workshops, it cemented enduring relationships with other humor writers like Emily Menez, who calls Durgin “magnetic and a comedic genius.”

Menez characterizes their first meeting as “friendship love at first sight,” and says that Durgin isn’t just “a delight to be around,” she’s also an inspiration.

“I was drawn to how fearless she is in writing about difficult personal topics,” Menez says. “Grief, loneliness, fear, she’ll write about our darkest emotions in such a relatable and profoundly funny way. She inspires me to be a braver writer.”

How to write humor

Durgin’s humor writing process is painstaking, deliberate and architectural, Menez explains.

“When Bryn is working on a piece, she takes in every detail around her, then workshops only the sharpest observations into her writing,” Menez says. “She’ll print out the rough drafts and slowly spin in more gold as she’s tightening the piece. This is how she creates something incredible like her New Yorker piece, ‘Your Slow and Sad Descent into Birdwatching.’ I can’t get over how brilliantly that piece flows and what it says about humanity while being absurdly funny and yet still about birds.”

Durgin herself likens her way of writing humor to the way she felt when she first got glasses as a young girl, after years of seeing every tree as “a kind of giant green blob.”

“I got glasses and all of a sudden I remember seeing every leaf, every detail,” she says. “Humor writing is this one big blob, but you put on different lenses and you see all these branches, all these tiny, little components, your vision is magnified.”

It’s a process she’ll try to share in her workshop, which is not about teaching someone to be funny, but rather teaching them to dissect and examine where the funny comes from.

“When I think about a humor piece, I’m seeing all the components, I’m building it,” she says. “It takes a lot of revision. I think that’s what a lot of people misunderstand. The difference between being funny and being funny on the page is revision.”

Her humor workshop is “really just about brainstorming ideas” she says, though she hopes attendees come away with tangible advice and tools. One exercise might be to write down three things you are angry or confused about, then using those as a starting point to “choose your own adventure.”

“What I love most about it is, if you tell me about a humor idea, I love being able to take a person’s idea and show them all of the other things they could do with it,” she says. “I’m not ‘Yes, and-ing,’ I’m ‘Yes, or-ing.’ You could do it this way, but maybe it’s funnier if you do it this other way, or this other way. The structure is a part of the joke.”

The thing she loves the most about the workshops is the exchange of ideas and the back and forth and brainstorming with other writers, much like what occurs in a “writer’s room” for a television series. Oh, and of course, the laughter.

“It feels like what I imagine some people feel on some kind of drug. When you’re just so dialed in and everyone’s paying such close attention. You’re not even thinking, it’s just pouring out of you. It’s really fun to be able to talk, share ideas and just laugh with people who are trying to do the same, very specific and weird thing.”

Currently, Durgin is working on a book – not humor – for which she’ll start a year long “incubator” practice in June. She also has “about eight humor pieces I need to finish,” but she’s not in any particular rush to get them into print because she likes to give her work time to “develop.”.

Time, revision and seasoning often are the keys to turning a piece from good to great, she says. After all, her “magnum opus” took six months.  Her father died in December 2021; the obituary she wrote for him did not appear until June of 2022.

“After he died, I went off by myself for three weeks and I just couldn’t do it, and I kept not being able to do it,” she says. “My mother is saying, ‘Bryn, we have to tell people!’ It became funny eventually. On the day he was cremated, the winter solstice – the day with the least light -- that’s when we finally told people.”

Now, when someone stumbles upon the obituary and is compelled to contact her about it, she’s grateful for the time she took with it.

“The biggest compliment I get is when someone emails me and says they just read my father’s obituary and they talk to me about how it made them feel,” she says. “This person who doesn’t know my dad whatsoever, but people say it makes them want to live their life differently. I think it is the piece I’m proudest of. “

As for that childhood vision she had of writing about “peaceful things?” These days she’s much more interested in writing about “what disrupts or disturbs – grief, longing, attachments, obsessions.” Though, she adds, the intention behind that early entry remains accurate: to stay close to the people she loves and notice the world around her.

“As a child, you can tell I pictured the writing life as very serene,” Durgin says. “Instead, at least in my experience, it seems to involve constantly vacillating between agony and ecstasy. Still, it's dreamy in that it's improbable, unstable and totally magical. “ 

“The Mechanics of Funny,” a humor writing workshop led by Bryn Durgin at Bookstore1, 117 S. Pineapple Ave. Sarasota. $75 (plus fees).  June 7, 2:00 pm - 5:00 pm. sarasotabooks.com/events; 941-365-7900.