When Samantha Allie Lesser agreed to go on a blind date with Michael Robert Wald in early May 2024, the idea had come weeks earlier while both were in Boca Raton, Fla., visiting their families for Passover. A friend of Ms. Lesser’s, who lives in the same gated community as Mr. Wald’s sister, suggested the match after meeting him.
“She told me, ‘I think you two would really hit it off,’” Ms. Lesser said. “‘He’s witty, and you’d have great banter.’”
They decided to meet once they were back in New York City and texted in the meantime.
On their first date at the cocktail bar Analogue, in Greenwich Village, “we talked about current events, history, politics, and conspiracy theories,” Ms. Lesser said. “Our conversation felt intelligent and flowed very naturally.”
They continued to Zinc Bar, a jazz club in Greenwich Village that Mr. Wald recommended for what he said were the city’s best espresso martinis. As the night ended, he stepped outside to hail her a cab. “One pulled up immediately,” he said. “She got in before I could even say anything.”
The next morning, Mr. Wald was debating what to text her when she beat him to it. “You were totally right,” she wrote. “Those espresso martinis were incredible.” He took it as a reassuring sign to ask her out again.
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Ms. Lesser, 32, is a lawyer at Becker NE P.C., a law firm with offices in Florida and the Northeast. She grew up in Boca Raton, Fla., and earned a bachelor’s degree in marketing management from Syracuse University, as well as a law degree and a master’s of law in taxation from New York Law School.
Mr. Wald, 30, is the senior vice president in renewable energy, power and infrastructure space at the Piper Maddox/LHi Group, a global executive search and recruitment firm. He grew up in Hewlett, N.Y., and has a bachelor’s degree in corporate innovation and entrepreneurship from Pennsylvania State University.
Mr. Wald planned two more dates within a week, and on the third, he knew he saw a future with her: “I told her we were getting married.” Ms. Lesser laughed and brushed it off.
The next month, in June 2024, the two became a couple. Two months into dating, Mr. Wald invited Ms. Lesser to join him on a two-week trip to Italy, where he was the best man at a friend’s wedding. The itinerary included an ambitious road trip with a rented vintage 1972 Alfa Romeo Spider.
“Whenever I mentioned the car, people said it would break down and that it was a terrible idea,” he said. “But I felt there were only two possible outcomes: We’d come out stronger, or we wouldn’t be together.”
He mapped an 800-mile drive from the Amalfi Coast to Rome. While everything was going smoothly, near the end of the trip, the car broke down on a winding road near the city of Benevento during a dangerous downpour.
They were stranded and soaked on the side of the highway, but were rescued by a passing mechanic and a group of teenagers. “It felt like ‘The Odyssey,’” Ms. Lesser said. “That people were being placed in our path to get us where we needed to go.” Five hours later, they made it to Rome, where that evening, Mr. Wald told her he loved her.
Mr. Wald proposed in Central Park on July 26, 2025, with an oval diamond ring. Both their families traveled from New York and Florida for the occasion, and they celebrated on the Upper East Side, starting with drinks at the Pierre, dinner at Scalinatella with their families, and a nightcap at Casa Cruz. The following month, they moved to the Financial District, where they currently reside.
They married on Jan. 21 by Yanfang Chen, an officiant at the Manhattan City Clerk’s office, with Mr. Wald’s mother, Heather Grey, as the witness. The couple celebrated afterward, on their own, over sushi and Tuscan red wine, as an ode to their trip to Italy, at Lure Fishbar in SoHo.
They will host a religious ceremony and wedding reception with 160 guests on Feb. 15 at the Boca Raton resort. But “doing the legal ceremony quietly in New York felt right to me,” Ms. Lesser said. “It was low-key and intentional, and it felt like the right way to begin our next chapter.”
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