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Past and Future Collide at Last Year’s Centennial Running of the Far Hills Race Meeting

You could say James Damiano was the biggest winner at last year’s Far Hills Race Meeting. Better than cashing in big on a bet, James got a “yes” when he popped the question to his girlfriend Bryn Dragalin in front of their friends and family…and 30,000 racegoers who watched from the jumbotron.

For Bryn and James, the larger-than-life proposal provided an unusual counterpoint to their otherwise domestic courtship. Bryn, 27, first noticed James, 29, at work. They were both training at NewYork-Presbyterian Columbia—Bryn as a nurse practitioner and James as an anesthesia resident. The two happened to be on the same dating app, and they agreed to go out on Nov. 14. 2020. Bryn said it was their first and last date—COVID-19 cases began spiking again so many bars were closed—and, with Bryn’s roommate gone and few friends left in the city, James moved into her apartment by the new year and signed onto the lease in May.

“Most couples, when you date at first, you see them one or two days a week, but he never left,” Bryn joked. “We had nothing else to do but hang out every day.”

Their relationship progressed so quickly that, by spring, when Bryn told her mother that James had casually mentioned his intention of marriage, her mother put a deposit down for a wedding date. After all, with COVID-19 causing couples to scramble to get dates—her mother wanted to be prepared. Bryn and James will be married on June 17, 2023, at Fiddler’s Elbow Country Club in Bedminster. Bryn notes that the wedding date itself has meaning: June or the sixth month of the year, plus 17 equals 23.

Long before Bryn got engaged, Far Hills has been a big part of her life. She’s been going to the event since she was in diapers and, because the race is right around her birthday, it has always served as a birthday celebration of sorts.

Though Bryn knew her boyfriend had purchased a ring, she wasn’t expecting a proposal when they headed to the race last October. Her family went to elaborate lengths to throw her off the scent—her mother even made up a fake UPS tracking number to get her to think the ring wasn’t ready yet. Besides, Bryn said that her fiancé is more of an introvert, and she didn’t expect him to propose in front of thousands of people.

On the big day, Bryn’s family told her she needed to look at the jumbotron at 1 p.m. to be part of a special 100th anniversary celebration. When Bryn got there, she looked up at the jumbotron expecting to see a photo of herself as a baby, but, instead, she saw of picture of herself with James.

“Everyone was making a circle around me and I thought that’s not me as a baby, Bryn recalled. “James was just staring at me. He forgot what he wanted to say and shouted: ‘I want to marry you,’ and I said, ‘OK.’ It was quick but memorable.”

For this year’s Far Hills Race, Bryn said that her family is bringing even more people, 40-50 guests as opposed to 20-30 in typical years, and they plan to make it into a mini-engagement celebration—moving the party back to their home.

Years from now, Bryn and James can look at videos, photos and lots of media coverage chronicling the happy and memorable occasion.

“All my family was there—my brothers flew in from Massachusetts and California,” Bryn said. “It was so special seeing everyone.”

Make sure you don’t miss out on all the action at this year’s Far Hills Race Meeting. Remember to renew your reserved tailgate spot today!

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