In 2017, Cassie transferred to Plainfield East High School. Despite the two meeting at the beginning of the year, Jason and Cassie would almost never interact with each other until January when they were both cast in the Spring musical. It was that semester where they developed feelings for each other, leading Jason to ask Cassie to prom at Disney World, on her 18th birthday. They both attended North Central College where their love continued to grow, and in their final semester, Cassie visited Jason in England during his study abroad trip. From this, Jason knew that Cassie was the one he would marry. He wanted to propose soon after graduating, but Cassie said "wait until I'm finished with grad school," so on December 20th, 2024 (one week after graduation), Jason got down on one knee in Madrid, Spain and asked Cassie to marry him.