Amaiya Briani Davis thinks she was in the grips of the woolly astrological stage known as “Saturn return” in the spring of 2018. “It’s this period before you turn 30 when a lot of change happens,” she said.
Ms. Davis, then 27, had started a new job as a music publicist and moved from her apartment in Midtown Manhattan to a place on the Upper West Side. Most destabilizing of all, in April, her boyfriend of almost two years, Matthew Carrington Durrae Wynter, abruptly broke off their relationship without much of an explanation. “It was hard for me to understand, why would you do this?” she said. “There was nothing fundamentally wrong at the time.”
Chalking her topsy-turvy late 20s up to the cosmos helped return her sense of equilibrium. But letting the stars decide whether Mr. Wynter was worthy of falling for a second time never felt like an option.
Ms. Davis, 33, and Mr. Wynter, 35, of Long Island City, Queens, met in the fall of 2009 at the University of Maryland when both were undergraduates, Ms. Davis a freshman and Mr. Wynter a senior. Before the two were introduced at a party given by a mutual friend, Ms. Davis had racked up a string of admirers.
“I had heard her name and the chatter,” Mr. Wynter said. “A lot of guys had mentioned this freshman, Amaiya, who was very beautiful.” Meeting her was proof they weren’t wrong, he said. But he made it clear he wanted no part in being on her shortlist of suitors. “He didn’t really interact with me, and it was a similar situation when we would run into each other after that,” she said. “He wasn’t very talkative.”
Ms. Davis took him for the quiet type. But Mr. Wynter, who is not shy, was standoffish in part because he had to be; he was in a long-term relationship.
They had practically forgotten each other by 2015 when Ms. Davis, who graduated with a bachelor’s degree in communication, and Mr. Wynter, whose bachelor’s degree is in American studies, started joining fellow “Terps” — short for Terrapins, the University of Maryland’s mascot — at New York City alumni meet-ups.
Mr. Wynter had moved to Harlem with a roommate to start a career in advertising. Ms. Davis was living with a roommate in Midtown. “A lot of Terps would get together to watch big sporting events,” Mr. Wynter said. “That’s how our friendship started.”
Moving to New York after college was, for Mr. Wynter, a homecoming. Now a real estate agent with Brown Harris Stevens, he grew up between two New York households. His mother, Claudet Whitmore-Dunkelly, and father, Linnel Wynter, separated when he was a toddler. His mother’s house was in Mount Vernon, his father’s in the Bronx. Both parents are Jamaican and made a point of settling in Jamaican-American enclaves.
“From the churches we attended to where we shopped, being Jamaican was very normalized for me,” Mr. Wynter said. “We had a strong sense of pride in our customs and culture.”
Ms. Davis grew up in Ellicott City, Md., alongside an older sister and brother. Her mother, Mariebel Davis, is Puerto Rican. Her father, Dr. Marvin Davis, an obstetrician and gynecologist, is Black. “My parents always emphasized the importance of owning both sides of our background,” she said. “They were always communicating to us that we should be proud of it, how beautiful it was.”
Her love of popular music — she is now the vice president of media and cultural impact and engagement at Republic Records — started early. At age 2, she was toddling around with her sister’s hand-me-down Walkman. Later, “I was Myspace obsessed and always finding music on Napster,” she said. “My siblings and parents ingrained that love of music for me.”
Her first home in New York after college was her sister’s apartment on the Upper East Side, where she crashed on the couch while looking for work. Meet-ups around the city with the Terps, including Mr. Wynter, were a way to start a social life. When Mr. Wynter invited her to a Fourth of July party in Long Island City in 2015, she accepted. “But there was no thought in my mind like, does he like me?” she said.
At the Fourth of July party, the fireworks that flew weren’t the romantic kind. Mr. Wynter was sorting out a relationship with an former girlfriend who didn’t like that he had invited Ms. Davis. “She thought there was some intent to it,” he said. “There wasn’t.”
That changed when Ms. Davis invited him via text to join her and some friends at No Malice Palace, a bar in the Meatpacking District, in January 2016. She expected him to come with friends; he had mentioned a group hangout of his own that night. But he showed up alone.
“Her text said, ‘You should come,’” he said. “I was trying to read between the lines, like, is this Amaiya telling me to come by myself?” Ms. Davis’s girlfriends peeled off when he arrived. “We started talking, and I remember he asked me, ‘So, what kind of guys are you into?’” she said. Two weeks later, they had their first date at Chef Yu, a Midtown restaurant. Days later, Mr. Wynter flew to a much-anticipated job interview at a tech company in Palo Alto, Calif.
“I had every intention of taking it if I got it,” he said of the job. “But when I was out there, Amaiya made a comment insinuating that she was going to be sad if I moved. That was the first moment I was like, oh, she likes me.”
He didn’t have to choose between his career and the new romance. The Palo Alto position never got liftoff. But the relationship was airborne upon his return. In September 2016, they bought tickets to Amsterdam to see Drake perform. When the concert was canceled, they took the trip anyway. At a stop-off in Paris, he asked her to be his girlfriend atop the Eiffel Tower.
Mr. Wynter is almost as mystified as Ms. Davis about why he broke up with her the following spring. But at the time he, too, was brushing up against 30 and dealing with life transitions. “I was trying to figure out a career change, what I wanted out of life,” he said. “I loved Amaiya very much. It was heartbreaking for both of us.”
Going to therapy, individually, helped. Ms. Davis started to accept the breakup was “a him thing, not a me thing,” she said. Mr. Wynter took a hard look at his motives. Before the split, “we were in a place where it was time to take things to the next level, and I wasn’t sure how to navigate that, and so I did the first thing that felt natural to me,” he said. “I ran.”
He adopted a cautious approach to winning her back. “I had broken her heart,” he said. “I had to be respectful and make sure the timing was right.” He waited until October 2019, when both were in College Park for the University of Maryland’s homecoming. Light conversation there got heavier back in New York, where they hashed out a fundamental difference in their backgrounds.
“He didn’t have a lot of examples in his past of long-term relationships where, when something’s wrong, you work through it together,” Ms. Davis said. By the end of that month, he convinced her he was invested in learning how. “He was very intentional about making the effort and spending time with me.”
She hadn’t forgotten what she called “an inkling” she had when he flew to California just after their first date in 2016. “It was this feeling we were going to be serious,” she said. “I think part of me always knew we would get back together.”
In November 2020, when the pandemic was raging, Ms. Davis moved into Mr. Wynter’s Harlem apartment. She was still unpacking when he tested positive for Covid. Days later, she tested positive. “That was a huge test for our relationship, because there was no vaccine at the time and a lot of uncertainty,” she said, noting a member of Mr. Wynter’s family had recently died of Covid. “It was so scary.”
Within a year, they had moved to their current home in Long Island City and Mr. Wynter was thinking about how he would propose. In 2022, on Father’s Day, he told Dr. Davis he wanted to marry Ms. Davis. Dr. Davis, who approved, kept the secret until Aug. 11, 2023, when Mr. Wynter proposed during a weekend getaway to Miami.
On Oct. 11, Ms. Davis and Mr. Wynter were legally married in a private ceremony for 15 guests by the Rev. David Nolan, a Roman Catholic priest, at the Church of the Blessed Sacrament on the Upper West Side.
The next day, they walked down the aisle a second time at Ravel, a hotel in Long Island City, where they welcomed 151 guests for an outdoor celebration. Ms. Davis wore an A-line wedding gown with a long train her mother and sister helped choose; Mr. Wynter wore an ivory tuxedo.
Leading the ceremony was Norman Earl Parker, Jr., a family friend of the Davises. He spoke about the pillars of happy marriages, including being present with each other and taking care to maintain their emotional and spiritual bond. He also “provided great advice about the importance of working through things together,” Mr. Wynter said.
With the city skyline glittering in the distance, the couple kissed, wiped tears and jumped a broom into their new, married life.
On This Day
When Oct. 12, 2024
Where The Upper West Side, New York City, and Ravel, Long Island City
A Love Letter to New York At a rooftop reception at Ravel, guests danced under the lights of the Queensboro Bridge and, after dinner, they were served New York-style pizza as a late-night bite.
Caribbean Roots The couple embraced their Caribbean heritage through music, with their first dance song, “Turn Your Lights Down Low,” by Bob Marley with Lauryn Hill, a tribute to Mr. Wynter’s background. “Lots of Salsa music played at the wedding — everyone was dancing!” Ms. Davis said. Tostones with mojo and Puerto Rican empanadas were served at cocktail hour. Jamaican black cake, which symbolizes joy and happiness, was given as favors.
Wynter is Here “Our saying and hashtag for the wedding was #WynterisComing, to mimic the ‘Winter is Coming’ line” from “Game of Thrones,” Ms. Davis said. At the second ceremony, the couple arranged for snow to fall as they recessed out.
Rhythm of Love The couple’s love of music found nods in their vinyl record-themed table seating chart and at key moments. David Michael Wyatt was accompanied by Sterling Strings quartet for the processional. Tyrone Benjamin performed during cocktail hour.
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