Oliver Brendan Gray had more than a decade of New York City dating experience under his belt in 2023 when he decided it was time to quit playing the field. “I was ready,” he said, to move into commitment mode.
So when Wendell Scott, his role model and mentor, started dropping the name of a single woman who had recently moved to the city, he paid attention. But when Gray politely asked for her phone number that November, Scott stonewalled him. “I was like, I’d like to fully explore this, to be set up,” Gray said. He didn’t know he’d have to prove himself worthy of an introduction to Kristen Taylor Smith.
Gray is the vice president and head of sports and client partnerships at The E.W. Scripps Company; Smith is a sports publicist for Prime Video and Amazon MGM Studios. Both gravitated to Scott, now the senior vice president of ad sales at Disney, early in their careers.
“I look at Wendell as an uncle,” Smith said. “He and I had kind of this familial tie, where he knew a lot of my mentors outside the workplace.” When she moved to Jersey City, N.J., from Detroit in 2022 to take a job in corporate communications at Disney’s New York offices, “he was always checking on me.”
Gray was more deliberate about getting Scott’s attention in the early 2010s, when he moved to SoHo after getting a bachelor’s degree in architecture at Tufts and deciding to pursue media marketing instead. “He’s a prominent figure in the industry,” he said. “One of my friends was like, ‘This is the person you should model your career after.’”
By 2023, both Gray and Smith were confiding in Scott about their lackluster New York City love lives.
“He took that as a mission to go solve this problem,” she said.
Smith, 30, grew up in Louisville, Ky., with a younger sister and later moved with their parents, Kristie Robertson-Smith and Andre Smith, to Detroit. She holds a bachelor’s degree in integrated strategic communication from the University of Kentucky and a master’s in sport management from Florida State University.
Gray, 38, grew up in Stamford, Conn., with an older sister and their parents, Sheri Wilson-Gray and O.B. Gray.
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The campaign Gray initiated in late 2023 to prove himself worthy of Smith’s contact info proved lengthy. “After 90 days of me being adamant about it,” Gray said, Scott agreed to relinquish her number in March 2024. But not unconditionally. “He made a specific demand for me to call her and not text. He was like, ‘She’s a lady. Do it right, Oliver. Do it right.’”
Gray, who had learned from Scott to honor his commitments, followed through. On the phone to Smith in late March 2023, “he said, ‘I would love to get to know you,’” Smith said. “In this era when everyone’s DMing, it definitely made a difference that he called me.” On April 2, they met at Barano, a now-closed Italian restaurant in South Williamsburg, Brooklyn. Smith had moved to Flatbush; Gray was living in Long Island City, Queens.
“We had a corner booth, and from start to finish, everything flowed,” Smith said. Before they said good night, Gray locked in a second date and a first kiss. At the start of June, with Scott’s approval, he asked her to be his girlfriend. Smith was way ahead of him — she told him it was about time he asked. “I was like, ‘yes, yes, yes,’” she said.
Gray was ready to propose that November when she moved into his apartment. But the engagement ring he saved up for months to buy stayed hidden until June 24, 2025, when he asked her to marry him on a vacation to Lake Como, Italy.
On Sept. 26, Smith and Gray married at Winnetu Oceanside Resort in Edgartown, Mass. Gray’s father obtained a one-day license from the state of Massachusetts to officiate what was supposed to be an outdoor lawn ceremony. But when a nor’easter roared up the East Coast the night before, their 105 guests were rerouted inside, to the venue’s restaurant.
When Gray’s father pronounced the couple married, Scott rose from his front row seat to place a broom Smith’s mother had fastened with white roses and pearls at their feet. For Scott, watching them jump it hand in hand brought a rush of emotion.
“It means so much to me to see Kristen and Oliver getting married,” he said, “especially knowing I had a small hand in bringing them together.”
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