There weren't many opportunities for in-real-life "meet cutes" during the pandemic but these two movie buffs did the next best thing: put it on their dating profiles. Sydney was scrolling through Hinge when she found Sam's profile. His perfect date night? "Cooking the same meal together with a nice glass of red wine and a classic film on TCM." A Turner Classic Movies enthusiast was the selling point for Sydney, and they spent many a socially-distanced first few dates watching everything from To Catch a Thief to Goodfellas over Zoom. When they finally met in person they spent their weekends making pizza from scratch, taking walks near Battery Park, hiking upstate, and pointing out all the dogs in the city. Their shared enthusiasm for trying new things, being outdoors, tinkering with Legos, and drinking bourbon dovetailed with discovered coincidences of mutual friends and Birchmont alumni. The rest, as they say, is history.

Sam and Sydney spent much of their early relationship walking around her Battery Park neighborhood, taking her dog Oakley along the waterfront when he was around, and taking their first picture together staring out at the Hudson near South Cove. On October 22, 2022, Sam planned a downtown date day, including an Oktoberfest at the South Street Seaport and dinner at an undisclosed wine bar. Sydney had an inkling as to what was going on but let the day unfold. After Oktoberfest with Sydney's sister Melissa (the maid of honor), Sam took Sydney for a walk around Battery Park at sunset. He tried to have them "take a picture" at the same spot they did two years ago, but another couple was sitting on their bench and told them to go away in the most colorful New York way possible. No matter, Sam took Sydney down to the bridge below their photo spot and asked her to marry him. Of course her answer was yes! Melissa was there to capture the moment along with a photographer. Sam took Sydney to dinner at Sant Ambroeus with their families in attendance. It was a perfect night.