Madeline and Jon met in the dining hall during their sophomore year at Georgetown University. While friends at school, they did not start dating until fate, by way of several large thunderstorms cancelling all Delta flights, intervened several years later. Two years after graduation, Jon was living in NYC but was frequently in DC for work. One evening, as a result of last minute flight cancellations due to thunderstorms and a suddenly free Friday night, Jon ended up at the same birthday party as Madeline. The two hit it off and began dating long-distance for almost two years. After countless Boltbus rides back and forth between NYC and DC, Madeline lured Jon down to DC permanently and the rest is history.

Mere months before coronavirus hit, Jon and Madeline were taking a long-planned vacation over the holidays to Belgium and France to celebrate Madeline graduating from Georgetown Law and passing the D.C. bar exam. In the city of Bruges, Belgium, Jon secretly planned for a local photographer to wait on a scenic canal bridge and take a photo of the moment when he proposed to Madeline. After careful maneuvering that day, Jon managed to lead Madeline to the bridge for the big moment. Madeline, whose fear of birds is a constant joy in Jon's life, immediately pronounced the bridge too close to a flock of beautiful swans and refused to take another step. After pleading and coaxing, Jon managed to get Madeline to the center of the bridge just as the photographer got into position. Madeline, still completely focused on making sure the beautiful swans kept their distance, was completely oblivious as Jon nodded at the photographer and got down on one knee. At this point, he had all of Madeline's attention. Madeline said "yes" and the photographer got an amazing live photo of the proposal full of the joy, surprise, and fear (of large birds) that made the moment so special.