In 1984, Andrew Gottlieb penned a note so long that it covered two pages of Elizabeth Alexandra Steuart Osha’s high school yearbook. In it, he matter-of-factly stated that they would one day get married. Four decades later his prediction came true.
The two met in seventh grade. Ms. Osha, who goes by Steuart, had transferred to the Dalton School on Manhattan’s Upper East Side. In what Mr. Gottlieb described as his “first suave move ever,” he asked the new girl if she’d go out with him. He treated Ms. Osha to a soda at a deli.
“As far as I knew, that was it, that’s what ‘going out’ was,” Mr. Gottlieb said. “I felt I had fulfilled my obligations.”
Mr. Gottlieb and Ms. Osha, now both 58, maintained a cordial relationship and were in the same social circles throughout the rest of their school years. They became close friends in the year or two before graduation.
“I was crazy about her,” he said. “But Steuart only liked me as a friend.”
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Both fondly recall evenings spent at Mr. Gottlieb’s apartment in Manhattan, where both grew up, watching television. One of their favorite shows was “Moonlighting,” starring Cybill Shepherd and Bruce Willis, which, amusingly, had a will-they-or-won’t-they plot hook.
“We used to think we were like those characters,” Ms. Osha said. “I was kind of earnest and ambitious. Andrew was the joker.”
Ms. Osha and Mr. Gottlieb’s lives diverged after graduation. She went off to Harvard to earn a bachelor’s degree in art history, then went on to receive a master’s degree in art history from Columbia. Mr. Gottlieb attended Wesleyan University and received a bachelor’s degree in art history and English literature.
Other milestones followed. “We both got married and were totally out of touch for 30 years,” Ms. Osha said. Each started families and later separated from their spouses. (Mr. Gottlieb’s divorce was finalized in 2021; Ms. Osha’s earlier this year.)
In 2019, Mr. Gottlieb, who lives in New Canaan, Conn., found himself racked with depression after his marriage faltered. He decided to look up an old friend whom he hadn’t seen in decades: Ms. Osha.
She was surprised to hear from him. Over the years, Ms. Osha, who lived in Manhattan and works as a world and American history teacher at Trevor Day School in Manhattan, had reconnected with former classmates online. But Mr. Gottlieb, a writer and producer of TV comedies and sitcoms who values privacy, eschewed social media.
The pair met for lunch at Rotisserie Georgette, the now-closed restaurant on Manhattan’s Upper East Side in April 2019. The meal lasted several hours.
“It was very unexpected, for both of us, how exciting it was and how much we had to say to each other,” said Ms. Osha, who was also separated by then.
By the end of lunch, Mr. Gottlieb invited Ms. Osha to his mother’s 80th birthday party the following weekend. “We’ve been together ever since,” she said.
It took another month for their relationship to turn romantic. “I somehow tricked her into kissing me,” Mr. Gottlieb said.
The couple enjoy going to the opera, taking walks and playing tennis. With help from Ms. Osha, Mr. Gottlieb was even able to join the Harvard Club’s squash team. “A great shame of my life is that I didn’t actually go to Harvard, but I’ve spent the rest of my life making it appear as if I did,” he said, jokingly.
Rekindling their timeworn connection prompted feelings of unexpected gratitude, Ms. Osha said: “When certain things didn’t go right or you had a disappointment in life, to kind of get another chance, you really do feel very lucky.”
In July, Mr. Gottlieb proposed on a tennis court at the Wadawanuck Club in Stonington, Conn. Ms. Osha was competing in an early round of a club tournament and Mr. Gottlieb came to cheer her on.
Before the match began, he walked onto the court to Ms. Osha, who had her racket in hand, got down on one knee and popped the question. She was rendered nearly speechless.
“You just said: ‘Andrew!’” Mr. Gottlieb recalled. “I said: ‘Steuart, you have to say yes so I can stand up.’”
This summer was marked by another event that did not warrant celebration. It was, as Mr. Gottlieb put it, “a fly in the romantic ointment.” He learned he had A.L.S.
“My diagnosis has somewhat changed my view of the future, but the diagnosis has also crystallized the far more important part of my future,” Mr. Gottlieb said, adding that the disease is progressing slowly so far. “Every second I get to spend with Steuart is just a miracle.”
The couple married on Nov. 16 in front of 120 guests at the New York Yacht Club in Midtown Manhattan. The Rev. Katharine Flexer, an Episcopalian minister at St. Michael’s Church on the Upper West Side, officiated. Ms. Osha was escorted down the aisle by her two sons, Pavan and Oliver Grover; Mr. Gottlieb’s daughters, Cristina and Alexandra Gottlieb, were designated ring bearers.
During the reception, Mr. Gottlieb’s stepbrother, Nick Scharlatt, and stepmother, Elisabeth Scharlatt, gave a dramatic reading of another letter Mr. Gottlieb wrote to Ms. Osha in 1984.
“I have lived a life of snarkiness, sarcasm and cynicism,” Mr. Gottlieb said. “And yet unequivocally, this was the greatest day of my life.”
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