Derek and Sydney connected on the dating app, Hinge, and met for their first date on the Tuesday before Thanksgiving. Their following dates included the Christmas themed cocktail bar at Rob Roy, watching Christmas Ships on Lake Union, celebrating NYE together at a friend's place in Capitol Hill, and attending Derek’s work holiday party. T’was the season for finding love for the couple, in Seattle!

Since the holiday season holds an extra special place in Derek and Sydney's relationship, it was only fitting that their engagement took place right after Christmas on their first trip to NYC together. After a day of wandering through West Village, Derek had a "spontaneous idea" to find a spot to check out the view of the Hudson River. He guided them to Pier 57 where they had the entire rooftop lookout to themselves and Derek popped the question!