Sidney and Brian first crossed paths at a nightclub in New York City, just before they both were set to head home to spend Christmas with their families. Following a couple weeks of messaging back and forth and their second encounter (under similar circumstances), Sidney and Brian finally had their first date. That initial date sparked an instant connection, and from that moment on, they were practically inseparable.

Brian spent months planning the perfect proposal day for Sidney. The two had some shopping planned in City Center, DC followed by a romantic dinner at Philippe Chow. When the two returned home, Brian lured Sidney to the rooftop of their apartment building with the promise of a "special champagne display", where they found a rose petal lined walkway and Marry Me in huge marquee letters. After she said yes, the couple were quickly joined by some local friends and Sidney's parents for a special champagne toast.