The first class of the day at Eureka College was a required Physical Education class, and no one knew whether or not the class would be held in the classroom on the upper floor or in the weight room on the ground floor. Jessica was at the top of the open stairwell, waiting for the door to be unlocked, while Stephen was on the ground floor, waiting for the weight room door to be unlocked. They were the only two people in the building at the time. Looking down from the top of the stairs, Jessica noticed that she and Stephen were wearing the same Pokémon printed t-shirt under their coats. Deciding to head down, she introduced herself and the two became friends almost immediately.
After a full year of being stationed abroad, Stephen returned home for the first time and took Jessica out for dinner at the Busy Corner in Goodfield, IL, a restaurant they had gone to many times before as friends after college. After a nice meal, the two continued on to Eureka College to take a nostalgic walk around their alma mater, remembering the time they spent there together, as well as sharing stories that neither one had told the other before. They even made time to share their first kiss while on campus as well. Then, as a final "cherry on top", the two made a stop at Uncle Bob's Ice Cream before returning home for the evening.
Planned out fully by Stephen, the couple first returned to Busy Corner for a lunch date, mirroring their first date. After the meal, the two returned again to Eureka College and headed into the Art building, where Jessica had spent most of her college career studying Graphic Design. Up on the third floor, where the Art Gallery is located, they came across a large whiteboard that had a gallery show sign on it, which was in fact a perfectly recreated version of Jessica's own Senior Gallery Art Show sign. Inside the gallery was a small rose bouquet in a vase, along with an Eevee plushie. Once inside, Stephen, while wearing the same shirt that they were each wearing on the day they met, proposed to Jessica, opening a pokeball with the ring inside. And Jessica said yes.