Stephanie Alise Fleischman knew she was “quite outside the norm” when Zachary David Kuperman was planning their trip to Italy in 2023.
“He’s just making a dinner reservation,” Ms. Fleischmann, 37, said with a laugh. So in her mind, since he’s a spontaneous guy, it could only mean one thing: A proposal was close.
Before the proposal, and even after it, Mr. Kuperman, 38, kept her guessing with one surprise after another, starting with a Lyft ride, not to the airport as he thought, but to his East 34th Street heliport Manhattan, where a Blade helicopter flew them to Kennedy International Airport.
Two years earlier, they had their first date on September 11, 2021, at the North Fork restaurant in the West Village, after meeting on the dating app Bumble a week before.
As they texted, they were certain that their paths had crossed before, and over dinner, it became apparent that they had led similar lives. They felt so comfortable that they ate from each other’s dishes.
“I’m 1,000 percent sure we were at the same parties,” said Mr. Kuperman, who grew up in Old Westbury, New York. Ms. Fleisman also knew some of his friends from the University of Pennsylvania, from which he graduated with an honors degree in history.
Mr. Kuperman, who received his law degree cum laude from Brooklyn Law School and enjoys reading cases for fun, is now a partner practicing commercial litigation at the New York law firm Abrams Fensterman.
“We like to joke about pulling up our Amex statements to see where we bumped shoulders,” said Ms. Fleischman, who lived across the street from him in Greenwich Village from 2016 to 2017. And, like him, took a cycling class. training at Switch Playground, an East Village gym that is now closed.
Ms. Fleischman, who grew up in Harrison, New York, is a product marketing manager at Google in New York. He graduated with honors from Vanderbilt with a bachelor’s degree in communication studies and human and organizational development. He received a master’s degree in communication management from the Annenberg School at the University of Southern California.
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After dinner, they took a Lyft to his best friend’s mansion in Williamsburg, Brooklyn, where they had a drink, and Mr. Kuperman showed her around. When they reached the basement, they had their first kiss.
Later, they went to a party at a nearby club and then had a late night meal at a food cart before the night ended around 5am.
“We’re not club people,” he said, but a week later after dinner and stopping at an East Village bar, they ended up at another club — a “Saved by the ’90s” disco party in Brooklyn. Bowl in Williamsburg, then sneaked into a private party at the Williamsburg Hotel.
On December 11, exactly two months after their first date, they made their relationship official during a late-night meeting of hearts at the bar at Indochine in NoHo.
In late February 2022, they vacationed in Mexico, where they saw a volcano erupt during the five-hour drive from Mexico City to Oaxaca, visited the ancient ruins of Teotihuacan, and stayed at a different hotel each night.
In a hotel room, when she sang the lyrics “I’ve finally found” from K-Ci & JoJo’s “All My Life,” she joined in. (It became their song and first dance at their wedding with a well-rehearsed dip).
“We had an intention to move on,” she said, and in May 2022, she moved into her Gramercy Park apartment.
In May 2023, when they arrived at the Hotel Danieli in Venice, waiting for her that morning, as she had planned, was a mockup of a Starbucks cup filled with the best tasting cappuccino she had ever had.
”He really loved me,” said Ms. Fleischman, who always started her day with a cappuccino of Starbucks skim milk with cinnamon powder.
That evening, they enjoyed highlights from various operas in a private box at Teatro La Fenice, Venice’s opera house.
“It was pure magic,” said Mrs. Fleischmann, who takes the groom’s name.
On May 6, 2023, after many other misadventures, he finally got down on one knee with a hired photographer at the Giardini della Biennale in Venice, where he recited a few lines from Walt Whitman’s “Song of the Open Road.” ”
On June 15, the couple married at the Rainbow Room in Midtown, before 192 guests, under a huppah decorated with a rainbow of flowers, and the groom wore an ivory tuxedo jacket. “Kind of like Humphrey Bogart in ‘Casablanca,'” he said, referring to one of his favorite movies.
Rabbi Eytan Hammerman, of Temple Gates of Prayer in Flushing, Queens, officiated.
In a surprising, romantic twist en route to New York from their recent mini-moon in Spain, they had to take a surprise flight from Madrid via Casablanca, Morocco, where they spent the night and enjoyed chicken tagine and Moroccan mint tea.
“We should have collected his white jacket,” Mrs. Fleischman said.
Before boarding the flight home they found themselves standing on the tarmac like the last scene of the movie.
“Looking at you, kid,” said Mr. Cooperman, reciting the famous line from the film. However, unlike the movie, they happily boarded the plane together.
