A Proposal in the Offing? Not so Fast.

Stephanie Alise Fleischman knew “it was pretty out of the norm” when Zachary David Kuperman planned their trip to Italy in 2023.

“He barely makes a dinner reservation,” Ms. Fleischman, 37, said with a laugh. So in her mind, since he is a spontaneous sort of guy, it could only mean one thing: A proposal was near.

Leading up to the proposal, and even following it, Mr. Kuperman, 38, kept her guessing with one surprise after the next, starting with a Lyft trip, not to the airport as she thought, but to Manhattan’s East 34th Street Heliport, where a Blade helicopter whisked them to Kennedy International Airport.

Two years earlier, they had their first date on Sept. 11, 2021, at the North Fork restaurant in the West Village after meeting on the Bumble dating app a week before.

As they texted, they were certain their paths had crossed before, and over dinner, it became obvious they had led similar lives. They felt so comfortable they ate off each other’s plates.

“I’m 1,000 percent sure we were at the same parties,” said Mr. Kuperman, who grew up in Old Westbury, N.Y. Ms. Fleischman also knew some of his friends from the University of Pennsylvania, from which he graduated cum laude with a bachelor’s degree in history.

Mr. Kuperman, who received a law degree cum laude from Brooklyn Law School, and loves 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 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, she took a circuit training class at Switch Playground, an East Village gym now closed.

Ms. Fleischman, who grew up in Harrison, N.Y, is a product marketing manager at Google in New York. She graduated cum laude with a bachelor’s degree in communication studies and human and organizational development from Vanderbilt. She 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 townhouse in Williamsburg, Brooklyn, where they had drinks, and Mr. Kuperman showed her around. When they reached the basement, they had their first kiss.

Later, they walked over to a party at a nearby club and then had a late-night bite at a food cart before the evening ended around 5 a.m.

“We’re not club kind of people,” he said, but a week later after dinner and stopping at a bar in the East Village, they ended up at another club — a “Saved by the ’90s” disco party at the Brooklyn Bowl in Williamsburg, and then sneaked into a private party at the Williamsburg Hotel.

On Dec. 11, exactly two months after their first date, they made their relationship official during a late-night heart-to-heart at the bar at Indochine in NoHo.

In late February 2022 they vacationed in Mexico, where they saw a volcano erupt during a five-hour drive from Mexico City to Oaxaca, visited the ancient ruins of Teotihuacan and stayed at a different hotel each night.

In one hotel room, when he sang the lyrics “I finally found you,” from the song “All My Life” by K-Ci & JoJo, she joined in. (It became their song and the first dance at their wedding with a well-rehearsed dip).

“We made an intention of moving forward,” he said, and in May 2022, he moved into her apartment in Gramercy Park.

In May 2023, when they arrived at Hotel Danieli, Venice, awaiting her that morning, as he planned, was a mock-up of a Starbucks cup filled with the best-tasting cappuccino she ever had.

“He really did love me,” said Ms. Fleischman, who always started her day with a Starbucks grande skim cappuccino 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 Ms. Fleischman, who is taking the groom’s name.

On May 6, 2023, after several other adventures, he finally got down on one knee with a photographer he had hired on hand 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 were married at the Rainbow Room in Midtown, before 192 guests, under a huppah decorated in 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 films.

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 an unexpected flight from Madrid via Casablanca, Morocco, where they spent the night and enjoyed chicken tagine and Moroccan mint tea.

“We should have packed his white jacket,” Ms. Fleischman said.

Before boarding the flight home they found themselves standing on the tarmac like the last scene in the film.

“Here’s looking at you, kid,” Mr. Kuperman recited the famous line from the film, but unlike the movie version, they happily boarded the plane together.