Jackson Clyde Patterson noticed Sydney Rose Robertson across the room at Freehold, a now-closed bar in Williamsburg, Brooklyn, while attending a friend’s birthday party with his brother.
“Oh, she’s cute,” he said when his brother mentioned that he knew Ms. Robertson and her group of college friends, who were not with their party.
It was April 2019, and Mr. Patterson didn’t realize he’d already met Ms. Robertson. Twice.
Their first encounter was a fleeting hello in August 2017 on the veranda at Villa Rosa in Oak Bluffs, Martha’s Vineyard, where their families vacationed, while both were hanging out with friends. He also had a girlfriend at the time.
Each graduated with a bachelor’s degree in economics; she from Wellesley College and he from Colgate University.
“Are you Tyler Patterson’s brother?” she asked when their paths crossed again in June 2018 at a mutual friend’s housewarming in Downtown Brooklyn.
“Nope,” he said, and after an uncomfortable pause: “He’s my brother.”
Mr. Patterson, then single, was “so full of himself,” she said, that she walked away.
During college, Mr. Patterson’s younger brother dated her Wellesley “little sister,” who was in the school’s Black mentorship program for new students.
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In 2019, at Freehold, Mr. Patterson and his brother walked over and invited Ms. Robertson and her friends to join their party.
“She looked stylish in a tweed blazer and vibrant red lipstick,” he recalled.
They drank, danced and “definitely made out,” he said.
Ms. Robertson, 29, who has a background in investment banking, has been working on a start-up health care investment platform called Lenox Dental Group, which is expected to debut this fall.
Mr. Patterson, 30, is now a software investor at Vista Equity Partners in Chicago, where the couple moved in July. He is also a member, like his father and hers, of Alpha Phi Alpha, the first Black intercollegiate Greek-lettered fraternity. Ms. Robertson is a member of Alpha Kappa Alpha, the first intercollegiate Black sorority.
When he suggested dinner at a sushi place nearby after the party, Ms. Robertson, who hardly knew him, insisted on chaperones — Mr. Patterson’s brother and a friend of hers.
“‘Oh, you’re going to fall in love with me,’” he recalled saying at dinner. “I was 24.”
“‘What makes you think that?’” she said, laughing it off.
“I laughed back,” Mr. Patterson added, “and said, ‘Watch.’”
After dinner, both went home to freshen up — he to Murray Hill and she to Harlem — and met again at 10:30 p.m. at a party one of his friends in the East Village was having, where she also knew people.
A couple of weeks later, they had a proper first date at Barn Joo, a Korean barbecue restaurant on Union Square, and parted with a kiss after he walked her to the subway.
“I was giddy,” Ms. Robertson said.
Two weeks later, they had dinner at St. Tropez, a French restaurant in Greenwich Village.
“I picked out the restaurant and insisted on paying,” she said. He said he was already wowed by her “strength, independence and intelligence.”
They continued the evening at Groove, a local jazz club. “We sat really close and talked into each other’s ear,” said Ms. Robertson, whose paternal grandmother, Lucille Dixon Robertson, a jazz double-bassist, played with jazz great Earl “Fatha” Hines.
When the pandemic hit in 2020, while he lived in Williamsburg, Brooklyn, and she in TriBeCa, a weeklong stay together at his parents’ house in Millstone, N.J., turned into a month and regular long visits.
“It was the height of racial reckoning,” he said, referring to the killing of George Floyd and its aftermath. “It was special to be together with such an intelligent Black woman.”
In June 2021, they both moved into different apartments in the West Village, and a year later, got one together nearby. Ms. Robertson, who loves to cook, made weekly Sunday dinners, usually pasta, for five to 10 guests, with pound cake or peach cobbler for dessert.
They soon set their sights on Harvard Business School, and spent hours at coffee shops studying together for the GMAT. In March 2023, they learned they were both accepted. Each has since earned an M.B.A.
He decided to propose in June 2023 before they moved to Cambridge, Mass., for graduate school and got her family in on the ruse.
“I invited him to my own proposal,” she said with a laugh, after her youngest brother told her he would be inducted into the athletic hall of fame at Riverdale Country Day School. She naturally invited Mr. Patterson.
Before the fictitious event, her mother dropped them off at the New York Botanical Garden for an exhibit by Ebony G. Patterson, a Black multimedia artist.
Instead, he got down on one knee in a gazebo in the Peggy Rockefeller Rose Garden, a nod to Ms. Robertson’s middle name.
On Aug. 16, after a downpour, Cole Brown, a childhood friend of the groom, who received a one-day officiant license from the State of New York, officiated before 275 guests at A Private Estate, an events venue in Germantown, N.Y. (Mr. Brown recently directed the Ralph Lauren campaign set in Oak Bluffs, in which the groom modeled.)
“There’s a lot of uncertainty,” she said of their new life in Chicago. “But the most important thing is certain. It’s Jackson.”
He quickly added: “And, it’s Sydney.”
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