Vicky had just moved to NYC full time when she was invited to a benefit cocktail party. Charlie was playing music for the party. Later that night, Vicky saw Charlie talking to her friend Nick, so she went over to talk to them. Charlie asked her to swing dance, and they became friends that night. After almost a year of a Jane Austen-esque, will-they-won't-they scenario, Vicky and Charlie attended the wedding of their friends Emma and Chris (now Charlie's best man) on January 5, 2019. Five days later, they went on their first date.

Charlie's original plan was to propose on top of the steps of the Philadelphia Museum of Art. However, there was a protest blocking the steps, so he had to come up with a new plan. He finally proposed in a park in front of the Basilica of Saints Peter and Paul, surrounded by flowers and a fountain. The park was empty except for one other couple, who quickly realized what was happening and started taking pictures. (Thank you, Tiffany and Kyle!) After returning to New York that evening, Charlie took Vicky to dinner at Buenos Aires Restaurant. Little did he know that it was the same restaurant where Vicky and her friends celebrated the completion of a 54-day Rosary novena for their future husbands several years earlier.