It’s hard to say Sarah Elizabeth Luciano and Samuel Bobley ever officially met, considering they had known one another all through middle and high school. But in 2008, when Ms. Luciano was a junior and Mr. Bobley was a senior at North Shore High School in Glen Head, N.Y., mutual friends invited them both to play Scrabble at lunch.
Mr. Bobley was excited about the invite. “Sarah was definitely on my radar as an attractive person I was interested in,” he said. And Ms. Luciano was excited by how much fun she had playing. “He’s annoyingly good,” she said. “I liked it, though. I knew he was smart.”
The two chatted on AOL Instant Messenger, and a few weeks later, it was Halloween. Mr. Bobley came to school dressed as Ms. Luciano’s favorite teacher, Brian Rodahan. He stopped by Mr. Rodahan’s history class and did a few imitations, which were well-received by the teacher and students, including Ms. Luciano.
“I liked how Sam was funny but not boisterous and obnoxious,” Ms. Luciano said. “He was more reserved but had really funny lines. He doesn’t need all the attention.”
That night, they went to a Halloween party at a mutual friend’s house. “Best decision I ever made,” Mr. Bobley said. There, they exchanged phone numbers.
In early November, they went on their first date. “Since Sam was a senior, he had a car,” Ms. Luciano said. “So, during third period, he drove me to Starbucks to get a chai latte — something I never got to do as a junior with limited off-campus privileges.”
On their second date, soon after, they went to see “Four Christmases,” the 2008 movie starring Vince Vaughn and Reese Witherspoon. In the car, he played the entirety of “A Rosie Christmas” by Rosie O’Donnell. “Pure romance,” Ms. Luciano said.
“That was how I wooed her,” Mr. Bobley said. They were officially a couple soon after and things were smooth sailing for the two years after they began college before they took a break and then got back together.
They took another break when Ms. Luciano moved to Los Angeles in February 2019 to pursue a career in acting. But, about a year later, Mr. Bobley went to California with a couple of friends to escape New York City during the pandemic.
“We rented an Airbnb in San Diego,” Mr. Bobley said. “I was chirping at her.”
Soon, those texts escalated, and in February 2021, they met for lunch.
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“We were fully in love with each other — it was like a 12-hour date,” Ms. Luciano said. “We were so happy to be reconnected. So, then, we were all out dating.”
She moved back to New York soon after to be with Mr. Bobley. “I technically lived on Long Island with my parents for the first couple of months, but stayed with Sam in the city most of the time.”
In September 2022, Ms. Luciano moved into Mr. Bobley’s apartment in the Woolworth Building in Manhattan’s TriBeCa neighborhood, where the two still reside.
Mr. Bobley proposed in August 2024. Ms. Luciano had been part of the ring designing process, which Mr. Bobley used to keep her from knowing when the actual proposal day might be.
The jewelry designer with whom they were working, Zaida Dua, “helped me with a little misdirection by telling Sarah the ring wouldn’t be ready for six or eight weeks.” But he already had it.
The couple went to BondSt sushi for dinner the night of the proposal. Their parents, siblings and best friends, unbeknown to Ms. Luciano, were decorating their apartment for a celebration.
Mr. Bobley had asked the doorman to be the photographer, and as they waited for the elevator to take them to their apartment, Mr. Bobley dropped to one knee. “I was shocked,” Ms. Luciano said.
Ms. Luciano, 33, is a content creator with 145,000 followers on Instagram and half a million on TikTok, as well as a comedian with a residency at Broadway Comedy Club and performances throughout the city. She attended the University of Delaware and was raised in Sea Cliff, N.Y.
Mr. Bobley, 34, is a founder and the chief executive of Ocrolus, a financial technology company focused on AI-powered loan underwriting. He holds a bachelor’s degree in communications and business from the University of South Carolina. He was raised in Glen Head, N.Y.
The two were wed at the Manhattan City Clerk’s office on March 25 by Yanfang Chen. Ms. Luciano’s parents, Elizabeth and Nino Luciano, and Mr. Bobley’s parents, Laurie and Peter Bobley, were in attendance.
On April 4, the couple had a celebration at Caesars Palace in Las Vegas with a ceremony led by Ms. Luciano’s older brother, Michael Luciano, with 150 people in attendance.
Marriage may be a gamble for some, but not for Ms. Luciano and Mr. Bobley. As the bride put it, “We’ve been crazy about each other since we were 16 years old.”
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