Aubrey Roemer Paints Portraits Of Montauk Locals, 400 By Summer’s End

Last Friday afternoon, Aubrey Roemer was barefoot, sleep deprived and feverishly searching for a lighter.The blond-haired, green-eyed artist doesn’t consider herself a smoker, she explained in between charmingly soliciting several employees at the Montauk Playhouse for a light. But in the heat of a project, her “chain-smoking” habits surface—setting her back about five cigarettes a day.

The source of her stress is “Leviathan,” an ambitious undertaking to paint 400 ethereal portraits from the salty, tourist-ridden hamlet’s 4,000 year-round residents—or 10 percent of the population, she explained, taking her first drag and breathing out a euphoric sigh.

After just a few puffs, she put out the cigarette, wiped her hands on her cutoffs and headed toward the back door, only to find her models pouring out.

“Are you guys leaving?” Ms. Roemer rhetorically asked the line of senior citizens, waiting to board their bus after visiting the community center at the Playhouse. Kissing an older gentleman on the cheek, she said, “Bye, honey.”

“Will you be back?” one of the women squeaked.

“Of course,” she cooed. “I didn’t get to paint you today. Next time.”

Satisfied, the woman smiled and climbed the stairs as Ms. Roemer walked back inside to her makeshift studio, where volunteer John Kessler was waiting. She took a seat in the chair opposite her subject, picked up a paintbrush and got to work.

For the first 11 minutes, they were nearly silent—an undeniable energy buzzing between them as Ms. Roemer quickly outlined his face on a wet doily, the blue paint leeching through the fabric onto a 150-foot-long scroll that keeps a washy monoprint of every portrait thus far.

Then, Mr. Kessler was no longer staring straight ahead. He was, without impetus, delving into nearly eight decades of memories—his Brooklyn upbringing alongside his twin brother; their days playing soccer and serving in the Marines side by side; his love for women, most of all his wife, who died almost two years ago; and his penchant for building model airplanes. Talk of a new Italian engine that recently cost him $189 lit up his blue eyes.

And all the while, Ms. Roemer nodded encouragingly as she captured his likeness, inside and out, not getting a word in edgewise.

That suited her just fine. The 29-year-old artist prefers concentration to chatter when painting portraiture, or in this case, she says, “curated anthropology”—people in a certain place during a certain time, yet still hailing to what has been and hinting at what will be.

“Does that make any sense, or does it make me sound like a pretentious asshole?” she asked later that afternoon, sitting outside a quintessential Montauk cottage where she is crashing with friends. “This is so fulfilling for me. And it’s a change of pace. Before, it felt like something was missing.”

Three months ago, life was not going as planned for Ms. Roemer. Her waitressing job was growing stale. Her love life had tanked. And around 2 a.m. during a party at her Manhattan apartment, she received an official rejection from Yale University’s MFA program—after being heart-wrenchingly close to getting in.

She was devastated. One week later, she found herself in Montauk for the very first time, ducking in from the cold at the Shagwong bar, the only open restaurant in town.

“Everybody was like, ‘Go to Montauk. The locals will leave you alone. They’re not even friendly. Just do you. Put your shit together, stop being a disaster and then come back to New York.’”

A couple days later, Ms. Roemer returned with a new circle of unlikely friends, her idea for “Leviathan” and a desire to leave the city behind forever. She quit her job, rented out her apartment and, by May 5, was living on the East End full time painting portraiture—a fascination of hers since she was a young girl growing up in Rochester, New York.

“It’s different for me,” she paused, her cool exterior cracking with vulnerability. “I’m, like, a foster kid, but not even exactly that. I don’t have parents. So, sometimes I think that contributes to the painting people thing.”

In 25 minutes, Ms. Roemer had finished Mr. Kessler’s portrait. “Boom, that’s a lovely little monoprint,” she said, peeling the doily off the scroll of fabric. “You’re number 93.”

The model stood up, straightening out his jeans with a yank of his belt as he looked down at the portrait—unable to stop a pleased, flattered smile from spreading across his face.

“You’ve sat the most still of anybody I’ve had today,” Ms. Roemer continued, commending him. “I’m serious. May all other eight people I have to paint today be as still as you.”

Then, with the fabric still wet, she rolled up the scroll, the faces washing into one another like an ocean wave. The project is not precious, she explained. It’s more rugged. She then packed up her gear and headed toward her basement studio—a 10-minute drive from the Playhouse.

She descended the stairs of the Montauk cottage and opened the door at the bottom. Dozens of blue faces on fabric, hanging from makeshift clotheslines and basement piping, stared back at her.

“Welcome,” she said, opening her arms to the dank, dimly lit space. “Yeah, it’s f---ing crazy, huh? Jesus. Do you want a seltzer?”

She had some time to kill. Her 4 p.m. appointment was running 45 minutes late, which was nothing new, she shrugged, opening a bottle of ginger beer for herself.

“I make a joke, but it’s not really a joke, that it takes longer for me to get the people into my studio than it does for me to actually paint them,” she said. “It teaches you a lot of patience.”

And she needed a lot of it for her next model, Jake DeSousa—just 3 years old and lucky he’s adorable. A bundle of energy, Jake made sure Ms. Roemer’s earlier wish, after painting Mr. Kessler, was not granted.

“Say ‘hi’ to Aubrey,” his mother, Trish Viscari, said to Jake, walking up the front lawn.

“Hiiiii,” Jake sing-songed.

“Hi,” Ms. Roemer said. “Let’s get you painted. You’re so cute.”

Jake smiled, unabashed, as his mother said, “He’s a flirt.”

“That’s okay,” the artist nodded. “So am I.”

The boy bounded down the basement stairs and into Ms. Roemer’s studio before slamming on the brakes. “Whoa,” he said, stopped in his tracks by the sea of faces.

“Can you look at me for 10 minutes, Jakey?” the artist said, coming in behind him and directing him toward a stool next to her worktable. “If you’re really good, I will give you candy or ice cream upstairs. I will reward you with sugar. Okay? Promise?”

“Ya. Promise,” he said. But just as quickly as he agreed, he slumped down on the table with a giggle, tongue out, playing with his toy cars—so beginning a long battle.

Despite all odds, Ms. Roemer had a complete—and accurate—portrait in about 20 minutes. His mother was thrilled, snapping a picture with her iPhone, while Jake gave mixed reviews.

“I don’t have blue hair,” he said, frowning. He was past his disappointment in a few seconds, seated on the floor with his toy cars. “You need to get your picture, Mommy!”

“Do you think I’ll be as difficult as you?” Ms. Viscari asked her son.

“That would be shocking,” the artist murmured.

In half the time, the mother and son were out the door—Ms. Viscari with photos of their two completed portraits and Jake with a handful of M&Ms. Ms. Roemer leaned against her table, surveying the dozens of faces staring back at her as she waited for her next model.

Just three months ago, she had been fantasizing about running a Chelsea gallery in Prada heels with a gaggle of gay interns hanging on to her every word. These days, she wants to make art, eat good food and surround herself with the people she loves.

That is simply enough, she said.

“You look into the eyes of 3-year-old Jake and, before him, an 80-year-old man, and he’s telling you, ‘It’s going to go by so fast,’ and he doesn’t even know how he got to be here,” she shook her head. “It makes you really think about how we ought to treat our lives, and it’s not something that’s expendable. It makes you think and readjust your value system.”

For just a moment, she lost herself in the eyes of her beloved Montauk subjects, staring calmly back at her.

“Leviathan,” the portrait project, will be on view at Eddie Ecker County Park in early September.