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.
