“Dating in New York can be so jading and demoralizing,” said Allegra Teresa Hanlon.
If films and television shows are any indication, it seems to have been that way for some time. It was the subject of Carrie Bradshaw’s musings in HBO’s “Sex and the City.” It was also reinforced in the 1989 romantic comedy “When Harry Met Sally,” when Marie (Carrie Fisher) proclaims to Jess (Bruno Kirby), while snuggled in bed, “Tell me I’ll never have to be out there again” — “out there” referring to the fraught world of New York dating.
For Ms. Hanlon and Thomas James Fitzpatrick, the complexities of the New York dating scene became a point of connection during their first date at Jackson’s Eatery in Long Island City, Queens, in June 2019.
“I’m so tired of dating in New York,” he told her while shaking his head.
Mr. Fitzpatrick had been living in Queens for three years. Ms. Hanlon was in New York for just a year, but that was enough for her to feel exhausted by the cycle of meeting new people, conversations fizzling out or ghosting. And, as Mr. Fitzpatrick put it, the air of, “You’re pretty good, but you’re not perfect, so I’m going to find someone else.”
He added: “It just felt so fast and transactional, and, I don’t know — it just felt not that romantic.”
Four years after their first date, Ms. Hanlon was able to place her arm around Mr. Fitzpatrick and recite the same phrase from “When Harry Met Sally,” her favorite movie, re-enacting the scene on the night of their engagement.
The couple first met on Hinge when Ms. Hanlon, 29, liked a picture of Mr. Fitzpatrick, 32, playing soccer. They were both college athletes: She played tennis at Cornell, where she graduated with a bachelor’s degree in English, and he played soccer at Bentley University, where he graduated with a bachelor’s degree in economics.
Mr. Fitzpatrick asked her out to Sunday brunch. After they finished their meal, they still had so much to talk about, so they popped into Woodbines, a bar nearby. After a few drinks, he walked her to the Vernon Boulevard-Jackson Avenue subway station, and he kissed her goodbye. “I was nervous, but I just went in for the kiss,” he said, “and it was great.”
He then went to Maine for two weeks for Fourth of July celebrations with his family, and Mr. Fitzpatrick, who typically disconnects from his phone during vacations, was not texting her much.
“I was super scared that he was going to forget about me,” Ms. Hanlon said, “and that I was never going to go on another date with this guy.” That’s typical of the dating scene in New York, after all.
She texted him: “I know you’re with your family, but I would love to see you when you get back from the Fourth of July vacation.” It was unlike her to propose a second date to a man, but she was certain about her feelings for him.
“I would love that, too,” he replied.
Their second date was at Manducatis Rustica, an Italian restaurant in Long Island City. After dinner, they stopped by his nearby apartment, where she noticed a massive Frank Sinatra poster in his room and a keyboard crammed against the wall.
Ms. Hanlon grew up in a music-focused family. Her father, Arthur Hanlon, is a pianist and a Sony Music Latin recording artist and her mother, Leila Cobo, is a music journalist in charge of Latin music coverage at Billboard. Ms. Hanlon, who grew up playing piano, loved that Mr. Fitzpatrick was also passionate about music.
They started seeing each other a few times a week. She took him to Jackson Heights, Queens, to try Colombian food at Arepa Lady and hole-in-the-wall restaurants like La Esquina del Camaron Mexicano.
Three months in, Mr. Fitzpatrick felt it was time to make it official. “I was starting to, as they say, catch some feelings,” he said. He didn’t want their relationship to “fall apart into nothing.”
They met at Court Square Diner in Long Island City in late August, and he was so nervous that he went to the bar next door and took a shot to loosen up. He sparked a conversation with the bartender, who told him, “You look nervous. What, are you going to ask a girl to be your girlfriend?”
That, he did, and Ms. Hanlon wanted the same thing. Over Labor Day weekend, she went to Coventry, Conn., where he grew up, to meet his parents for the first time. Later that month, he visited her hometown, Key Biscayne, Fla., to meet hers.
Together, they often enjoyed breakfast on weekends, strolled around Central Park and frequented new bookstores and farmers markets. Though things were going great, in August 2021, Mr. Fitzpatrick made the decision to put their relationship on pause.
“The pandemic in general made me think, ‘What are you doing with your life?,’” he said. He was second-guessing his career in finance and wanted to pursue his passion for winemaking. He quit his corporate job in finance and went to Sonoma County, Calif., for three months, where he was a harvest worker for DuMOL Winery in Windsor, Calif.
“I was like, ‘What do you mean?,’” Ms. Hanlon recalled thinking when he first broke the news to her. “‘You still want to be with me? But you also expect me to hang on and wait around?’”
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Ultimately, their time apart “saved” their relationship, she said. During the pandemic, the two had become codependent on each other since they weren’t able to see other friends or partake in the hobbies that they usually do. During the break, she followed some advice to “take this time and rediscover who Allegra is, what Allegra wants and what Allegra likes to do,” Ms. Hanlon said.
He returned to New York confident about his career, living situation and relationship. And she learned that she values her independence — she likes to be social and go out to salsa clubs with friends. (Mr. Fitzpatrick is more of an introvert.)
The night that he landed in New York, in November 2021, they met for dinner, shared their reflections and got back together.
A year after the break, in late 2022, the two visited Cali, Colombia, where Ms. Hanlon’s 95-year-old grandmother resides. “I really badly wanted him to see that side of my heritage and understand my culture,” said Ms. Hanlon, whose mother is Colombian and father is Irish. Mr. Fitzpatrick, whose parents are both Irish, played cards with her grandmother, practiced his Spanish and took salsa lessons with Ms. Hanlon.
On Nov. 11, 2023, Mr. Fitzpatrick proposed at Grand Central Terminal, after he tricked her into thinking they would be headed to a hike in the Hudson Valley. They met at the terminal’s clock tower, and in the middle of the chaos, Frankie Valli’s “Can’t Take My Eyes Off You” started playing from a speaker. Ms. Hanlon looked up to see their parents and her friends holding letters on the balcony that read, “Will you marry me?” Strangers gathered around them and applauded.
In March 2024, the couple moved into an apartment in Carroll Gardens, Brooklyn. Mr. Fitzpatrick is now a finance manager at Warner Music. Ms. Hanlon is a marketing manager at Victoria’s Secret Pink.
On Jan. 18, the couple were married at St. Agnes Catholic Church in Key Biscayne in front of 175 guests. The Rev. Juan Carlos Paguaga, a Catholic priest, officiated. Peter Nieto, a singer from Miami, performed “Ave Maria.”
The musical performances continued at the reception that followed at the nearby Ocean Club.
A bagpipe player played at the entrance of the club. Ms. Hanlon’s father performed a Latin rendition of “Danny Boy,” an Irish song, on piano.
A local band played an assortment of classic American wedding songs and classic salsa tunes, including “Cali Pachanguero,” an ode to Ms. Hanlon’s maternal hometown.
The Colombian singer Fonseca made an impromptu performance, and a D.J. from Fiesta Bresh, an international party collective that originated in Buenos Aires, also took the stage.
The couple read their vows to each other the morning after at a bed-and-breakfast in Islamorada, Fla., where they had a “mini-moon.”
“There’s so much peace in knowing that you have your person that’s going to be there for you no matter what,” Ms. Hanlon said.
“That’s how I feel,” she continued. “I have a peaceful heart.”
On This Day
When Jan. 18, 2025
Where St. Agnes Catholic Church, Key Biscayne, Fla.
Handwritten Letters Ms. Hanlon wrote a personalized letter by hand to every wedding guest that tied elements of their history together.
A Colombian Sensation In a letter to Fonseca, a friend of her parents, Ms. Hanlon mentioned that his ballad “Te Mando Flores” was her anthem in high school when she fantasized about having a boyfriend. The song is about sending a woman flowers and waking her up with kisses every morning. She hoped that she would one day meet the person who feels the same way about her. “I wrote in the letter that it meant everything to me that I did end up meeting this guy,” Ms. Hanlon said. The message touched Fonseca, and he felt compelled to sing the song that night, though he had not planned on performing.
‘La Hora Loca’ The final hour of a Colombian party is known as “the crazy hour.” At the reception, Fiesta Bresh played music from J Balvin and Abba and brought out a person dressed as a gigantic red bear. Guests danced the conga and struck mini tambourines that read “Allegra and Tommy,” which were designed by the wedding planner, Natasha Benitez. During the last song the D.J. played, “Mr. Brightside” by the Killers, he descended from the booth and danced with guests as they shouted the lyrics.
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