After moving to Philadelphia in the summer of 2018, Chris and Colleen had their first date at Rosy's Taco Bar. They quickly bonded over a mutual love of puns, sharing meals, and lightheartedness. Once they worked their way through Philly's restaurants, they spent 2020 travelling and trying new hobbies. Chris taught Colleen how to ski in Utah, and Colleen convinced Chris that hiking up a mountain was just as fun as skiing down one. They covered mountains and lakes from Pennsylvania to California and eventually landed in Austin, TX. In 2021, Chris took Colleen to Tuscany. He wined, dined, and attempted to propose to Colleen, who said yes before he could ask.