John and Samantha met while both studying at the University of Pennsylvania. Samantha was completing a post-baccalaureate prior to matriculating to medical school, and John was completing his law degree. They were first introduced through Samantha’s roommate, who was one of John’s law school classmates. Samantha often accompanied her roommate to law school events, one at which she and John would eventually meet. John expressed interest, but at the time Samantha declined to focus on her studies. Two years later, they reconnected on social media. Samantha posted Childish Gambino lyrics, and John took the opportunity to send a playful message: "Would you let Childish Gambino’s ghostwriter treat you to drinks?" Amused by his humor, Samantha agreed. Their first date was at Charlie Was A Sinner in Philadelphia, where they sat and talked for hours. They quickly realized how much they had in common, from sharing the experience of being the oldest of five siblings (each with two sisters and two brothers), to their mutual love for music. That summer, they spent nearly every day together, and the rest, as they say, is history.

John asked Samantha to dinner on the last night of their vacation in Italy. During their walk home, he offered Samantha his sweater to keep warm. As they approached the Fontana del Tritone in Rome’s center city, John mentioned that he forgot his wallet in the restaurant. Apparently panicked and patting his legs, John asked her if his wallet might be in his sweater pocket. When Samantha went to check, she noticed a small rectangular box. After Samantha removed the box from the jacket pocket, John opened it to reveal a ring, dropped down to one knee and popped the question.