Gavin and Olivia met at the Gray-New Gloucester High School Homecoming Dance during Olivia's senior year of high school. Olivia asked Gavin to dance, and despite her "interesting" dance moves, he agreed. Over eight years later, Olivia still cannot dance and Gavin still loves her anyway.

After months of planning, Gavin asked Olivia to marry him at Great Diamond Island off the coast of Portland, ME. Olivia attempted to foil the proposal several times by refusing to enter the private beach where there were no trespassing signs posted. Nevertheless, Gavin convinced Olivia to break the law, and he asked her to be his forever partner in crime.