Chase and Jessica's story started as a modern day love story. They met on an online dating app. They talked online for around 8 months before agreeing to meet in person. This was during the beginning of Covid, and as everything was shut down, Chase drove to Plymouth to meet Jessica and ended up meeting Jessica's entire family as well. They started officially dating three weeks later.

Chase joined Jessica on her family ski vacation to Steamboat, Colorado. Chase had never been skiing before. His original plan was to propose to Jessica on her favorite ski run, however, during a ski lesson Chase was told by an instructor that he was a "danger to himself and others". Chase instead decided to offer to go snowshoeing. They then went on a beautiful hike and as Jessica was posing for a picture, (special thank you to Robin McHugh for documenting the moment) Chase got down on one knee.