Kerry and James met in Buffalo, New York in the summer of 2018. Kerry was spending her final few weeks in Western New York before starting graduate school in Massachusetts, and James was visiting his family and friends in between work assignments as a traveling physical therapist. Their first date took them through a jazz festival at Delaware Park, the Buffalo Garden Walk, Lloyd Taco Factory, the Elmwood Village, and Café Aroma. They couldn't stop talking with one another the whole time. Less than an hour after the date ended, they planned the next one. After two more dates, James went to work in Hawaii for three months, and Kerry started graduate school. Although most love stories would end when the two characters move 5,000 miles apart, the opposite happened with Kerry and James. They missed each other a ton and made plans to FaceTime three days per week. With a six-hour time difference, Kerry was typically getting ready for bed and James had just pedaled his bike uphill to get home from his shift at the hospital. Neither of them minded, and they ended up talking for two or three hours at a time. James returned home in November, raced to see Kerry on his second day back, and asked her to be his girlfriend as soon as he could. James took a new job in Buffalo while Kerry finished her master's degree. Despite the distance between them, Kerry and James made the most of the time they could spend together, including trips to Boston, Montreal, Maine, Toronto, Portland, Seattle, Rhode Island, Amsterdam, and South Carolina. In February 2020, while on a weekend trip to Vermont, James asked Kerry to marry him at Shelburne Farms on top of a hill overlooking Lake Champlain and the Adirondack Mountains. A group of cross-country skiers passing by took their photo, and the whole group celebrated with shot glasses made out of ice.