It all began when David spotted a photo of Sydney and her dog Chunky wearing matching Easter Bunny ears on the dating app Hinge. At the time, Sydney was working on the Olympics and David on his new company, but they managed to squeeze in a first date at Lantern's Keep, a cocktail bar in NYC. It was Sydney's first real date ever and she was so nervous she can hardly recall being there, but they both could never forget what an enchanting evening it had been. Their second date was around Valentine's Day, and David decided to bring Sydney a small bouquet of flowers. When he went to pick them up from the florist, he called his cousin Audrey in a panic; the florist had been "helpful" and given him a bouquet that was almost too big to carry. Surprisingly, this didn't scare Sydney away, and they had their third date soon after. While they were sitting together after dinner, Sydney asked David if he was comfortable. He replied, "I couldn't be happier," which has defined their relationship ever since.

After only a few months of the best thing they’d ever had, they both knew they were meant to be together forever. David planned a surprise proposal on New Year's Eve with the help of Sydney's sister Lydia, her parents, and one of her best friends Claire. They told Sydney that her family was going to a fancy hotel to celebrate her parents' wedding anniversary. David's cousins helped him pretend to be in New Orleans with his family, while he, his parents, and many of Sydney's friends and relatives secretly gathered in Baltimore. The big night arrived, and Lydia took Sydney to the rooftop restaurant where David was waiting with a ring crafted from his grandmother's diamond and a box of tissues. She said yes! They went to dinner, where all the surprise guests were waiting. Afterwards, they all returned to their hotel suite to celebrate the new year and watch the fireworks over the harbor from the stunning view. The next morning, while cleaning up the "glitter on the floor after the party,” they already had the same dream for their wedding: to tie the knot a year later on New Year's Eve.