Jessica does not remember the first time she met Shane despite being introduced by (now bridesmaid) Grace Maginn the first week of senior year. Fast-forward to Senior Week at Notre Dame. Jess and Shane had all but graduated and were enjoying the last week before concluding their four years in South Bend. No more classes, no more tests, all that was left were days relaxing and nights out with friends. On the Tuesday before graduation, these two found themselves walking home in the same group of friends and Shane figured that then would probably be the best time to (re)introduce himself to "Grace's Hot Friend Jess". What Jess had not yet realized was that the tutoring group she had started volunteering at a few months prior was the same one Shane had volunteered with for four years. It was there Shane first witnessed Jess's kind nature, quiet patience, and absolute talent with children. Upon sharing these observations with her, Jess's heart melted and the two talked the rest of the night as they walked around the lake. They decided to start dating a week later, the same day they parted ways for home.

After weeks of careful coordination with Jess's mother to have a ring created using her original diamond, the Trinkl family plus Shane set off for an Italian vacation. On the 2nd day in Florence with some downtime before dinner, Shane suggested the group take a walk up to the Piazzale Michelangelo. This particular piazza sits atop a hill overlooking Florence and provides arguably the best possible view of the city and surrounding countryside. Jess's family (all in on the proposal plan) each made excuses for why they would just meet up at dinner instead. Three quarters of the way up to the piazza sits a large quiet garden, a serene contrast to the hundreds of bustling visitors just above. Shane and Jess made their way through the garden finding a stone wall to sit on and take in the beautiful scene. As sunset neared, Shane turned the conversation more sentimental (tipping Jess off slightly) and finally asked Jess if she would agree to marry him. Her hand shook as she said yes and helped Shane put on her new ring. Jess's family was of course nearby and excited to celebrate a new addition to the family.