Love on the Rock: Love, Loss and the Miles Between

On Shelter Island, love stories aren’t just about two people. They are often about other Islanders watching, guessing, and sometimes weighing in. For Mary Larsen and James (Jimbo) Theinert, the Island wasn’t just their backdrop, it was the gentle hand, and occasionally the push, guiding their slow journey from church pew buddies to soulmates. 

Their story begins Christmas Eve 1990 on a crowded church pew at Our Lady of the Isle. Mary was two years old, on the brink of a toddler meltdown. Jimbo was nearby with his family. His mom, Chrys, plucked Mary from the chaos and set her next to Jimbo’s crew, handing over a lineup of toys and snacks. Neither remembers a connection, of course, but it planted the seed that would take decades to bloom.

The two attended kindergarten at Shelter Island School together, though Mary admits she doesn’t really remember Jimbo from those early days. “I was preoccupied avoiding the biter in our class,” she laughs. 

Life quickly separated them, with Mary attending Stella Maris School in Sag Harbor in 1st through 8h grade, while Jimbo remained at Shelter Island School. Still, their paths crossed in Sunday school, during First Communion, and again at Confirmation.

Jimbo attended The Ross School in East Hampton for 9th grade, but by 10th grade, the two finally landed in the same place at the same time, albeit on opposite ends of the social spectrum. Jimbo was the friendly, social math guy; Mary was the quietly artistic type, more comfortable in the art room than the cafeteria. “I think I really noticed Mary in 10th or 11th grade,” he says. “There was just something about her … creative, passionate, beautiful, a little different from everyone else.”

They ended up in a few electives together. One Halloween, they joined forces for a school “Anything Goes” competition, going all in as Sesame Street characters. Mary built an elaborate, sweaty Snuffleupagus costume from an old quilt draped over a laundry basket. Jimbo, as Big Bird, painstakingly glued yellow boas to a sweatshirt and spray-painted flippers orange for feet. 

“We were both willing to be ridiculous,” Jimbo says. “And we showed up for each other in that way.”

He also wasn’t shy about his crush. In their senior year, when the school newspaper asked students what they wanted to be when they grew up, Jimbo answered: “Mary Larsen’s husband.” Mary was mortified, convinced he was teasing her. But she kept the news clipping.

Despite the mutual attraction, they never dated in high school. On graduation night, Jimbo finally asked Mary out, and they spent that summer together. But Mary, wary of long-distance heartbreak, ended things before leaving for Savannah College of Art and Design. “I’d seen too many older friends crash and burn with college relationships,” she says.

Over the next four years, they fell into a seasonal rhythm — brief encounters on Shelter Island during school breaks, some warm, some awkward. One summer, Mary returned with a college boyfriend, who, to Jimbo’s dismay, worked both at their shared restaurant job and at his South Ferry shift. “I thought Mary and I would pick up where we left off,” Jimbo says with a grimace. “Instead, I had to see this guy at two jobs.”

By 2009, both had graduated — Mary from Savannah College of Art & Design and Jimbo from SUNY Albany — and had returned home. Mutual friends nudged them into the same social circles, and slowly, something rekindled. This time, the timing was right. They dated quietly, often on the South Fork, away from the prying eyes of the Island. Beach picnics at Sagg Main with sandwiches from Espresso, dinners in Montauk, and long drives gave them the space to grow close without the weight of everyone else’s opinions.

Then, in June of 2010, everything changed. Jimbo’s older brother Joe — his best friend, travel partner, and quiet cheerleader for the Mary relationship — was killed. Joe had been serving as First Lieutenant in the United States Army’s 10th Mountain Division, and was deployed to Afghanistan. He came under fire while leading his platoon on a foot patrol near Kandahar and was killed by an improvised explosive device (IED). “The loss of Joe was crushing. The light went out of Jimbo,” Mary recalls. She’d always known him as the goof who kept everyone smiling. Now there was a heaviness that wouldn’t lift.

Jimbo soon told Mary he wanted to take an open-ended cross-country road trip after finishing graduate school. “I didn’t know if I’d come back,” he says. “I just needed to get out, breathe different air.” Without hesitation, Mary said, “Yes.”

In July 2011, they packed their Volvo station wagon and set off. For 10 months, they camped in national parks, washed socks on the hood of the car, and learned to live out of a trunk. In campgrounds, they were often the youngest by decades. Retirees would ask how two 20-somethings had managed to hit the road so early in life. “We’d just look at each other and say, ‘Why wait 50 years?’” Jimbo remembers.

It was, as Jimbo calls it, a crucible. “You’ll either come back broken up or married,” friends told them. They returned neither, but they returned close: 10 months together in tight quarters stripped away any illusions. Small annoyances simply didn’t matter anymore. “When you’ve been drying socks on a car in the desert, you don’t care if someone leaves their laundry next to the hamper,” Mary said.

Back home in 2012, fate handed them an anchor. One of the two Shelter Island School math teachers had retired, and Jimbo landed the coveted position. They rented a home in Shorewood with friends and “played house” for a year. The life they’d tested on the road worked just as well under one roof. Mary eventually found her way to the Shelter Island Library, combining her love of libraries, art and kids in her role as assistant to the children’s librarian.

By the summer of 2013, Jimbo had saved enough to propose. He had bought a vintage diamond and sapphire ring from his Aunt Rosie’s family jewelry store and tricked Mary into going on an adventure to Acadia National Park in Maine, where he proposed. That fall, they bought their home, even before setting a wedding date. “We wanted to cement our future here,” Jimbo says. 

They married at Our Lady of the Isle in 2015, hosting the reception with over 400 guests in the backyard of their 1860s farmhouse, sprinklers still running the morning of the wedding to coax the grass into lushness.

Mary and Jimbo now have 10 years of marriage, and their daughter Acadia, seven, and son Archie, five, beside them, each a mini-me and the center of their lives. The couple’s guiding principle is simple: time is the most precious currency. Every decision — career, travel, family — is weighed against one question: Will this give us more time together as a family doing what we love? 

What does the family love doing most? “Friday night beach dinners with our friends and all the kids. We pick up pizzas and head to Crescent or Wades and play games and hang out. It’s the best,” Jimbo says.

Mary adds that the cross country road trip, born of grief, gave them the gift of perspective. “Losing Joe taught us how quickly life changes. We’ve carried that with us ever since. Don’t wait. Do the thing. Take the trip. Be with your people.”

From a kindergarten classroom to a cross-country odyssey, from a quirky high school crush to a marriage forged through family, joy and loss, Mary and Jimbo’s love story is proof that sometimes, the best things are worth the wait. And the miles.

This Saturday, Sept. 6 at 4:30 p.m., Strongpoint Theinert Ranch will hold its annual Ferry Cruise to honor and remember the service and sacrifice of First Lieutenant Joseph J. Theinert, and to raise funds for its ongoing programs for military veterans and Gold Star families. Tickets are available at StrongpointTheinert.org