In the fall of 2014, Jackie and Alex, both music education majors at Northwestern University, took a class called "Vocal Pedagogy." For one project, the students in the class had to accompany each other in vocal performance (keep in mind: neither Alex nor Jackie consider themselves singers.) They had their first performance together with Jackie singing the Puccini aria, "O mio babbino caro," and soon realized that they had an effortless chemistry in performance.

Following the initial musical courtship, Alex took Jackie out to a beautiful dinner at the Evanston steakhouse, Pete Miller's. From then, their relationship blossomed; only weeks later, the two traveled by car across the Canadian border for a romantic getaway in Toronto. Then, for their spring break, they escaped to Ireland. Wandering around the streets of Dublin, it felt as if they had known each other for years.

In February, Jackie traveled to New Jersey to see her newborn niece, while Alex traveled to Chicago for his Masters audition at Northwestern University. They planned a rendezvous in downtown Chicago right before the audition, with Jackie under the assumption that Alex would be focused on practicing for his audition. As a "joke," they went to a special jeweler to try on engagement rings, though Jackie didn't think anything of it. Secretly, Alex had brought along the ring that he bought for Jackie four years earlier in Ireland. At the restaurant, The Aviary, and in full view of the kitchen staff and waiters, Alex got down on one knee (somewhat awkwardly and in the corner of the room), and proposed. Even though Jackie was shocked, it was a pretty quick "yes", met with cheers from the restaurant staff.