After more than a decade navigating the New York City dating scene, Oliver Brendan Gray decided in 2023 that he was ready to pursue a committed relationship. Encouraged by a trusted mentor, Wendell Scott, Gray sought an introduction to Kristen Taylor Smith, a single woman recently relocated to the city. However, securing her contact information proved more complicated than Gray anticipated.
Scott, now senior vice president of ad sales at Disney and a respected figure in the media and advertising industry, initially withheld Smith’s phone number, requiring Gray to demonstrate his earnestness. “After 90 days of me being adamant about it,” Gray said, Scott finally agreed to share the contact details in March 2024—but with a condition: Gray was to call Smith rather than text, emphasizing respect and traditional courting.
Gray, who is vice president and head of sports and client partnerships at The E.W. Scripps Company, followed Scott’s instructions and called Smith, who was then a sports publicist for Prime Video and Amazon MGM Studios. Smith recalled, “In this era when everyone’s DMing, it definitely made a difference that he called me.” Their first meeting took place on April 2, 2024, at Barano, an Italian restaurant in South Williamsburg, Brooklyn. Both living in nearby New York City neighborhoods—Smith in Flatbush and Gray in Long Island City—they hit it off immediately. Before the evening ended, Gray had secured a second date and their first kiss.
Smith, 30, originally from Louisville, Kentucky, had recently moved to Jersey City, New Jersey, after working in corporate communications at Disney’s New York offices. She holds degrees from the University of Kentucky and Florida State University. Gray, 38, grew up in Stamford, Connecticut, and made a career transition from architecture to media marketing. Both had leaned on Scott as a mentor early in their careers, with Smith describing him as an “uncle” figure who had maintained a supportive presence during her move to the New York area.
By June 2024, Gray and Smith had become a couple, with Scott’s blessing. The relationship progressed quickly but thoughtfully. Gray was prepared to propose by November when Smith moved into his apartment, though he waited until June 24, 2025, to pop the question during a vacation in Lake Como, Italy.
Their wedding took place on September 26, 2026, at Winnetou Oceanside Resort in Edgartown, Massachusetts. Originally planned as an outdoor ceremony, severe weather forced the celebration inside the venue’s restaurant. Gray’s father officiated the service under a special one-day license issued by the state.
Among the 105 guests was Scott, who participated in a symbolic broom-jumping ritual—a tradition representing the couple’s commitment—by placing a forehead-adorned broom at their feet and witnessing them leap hand in hand. “It means so much to me to see Kristen and Oliver getting married,” Scott said. “Especially knowing I had a small hand in bringing them together.”