Olivia and Tom have known each other since they were fourteen years old, having met in high school (Olivia attended the all girls school, and Tom the all boys school). They became quick friends, with Olivia often trying to set Tom up on dates with her girlfriends. Tom played along, all while hoping that eventually, Olivia herself would want to go out with him. The two would make each other weekly CDs, edit each other’s homework for their respective schools, and spend hours swapping stories. When Olivia caught pneumonia the week of Valentine’s Day their junior year, Tom came to cheer her up armed with a Fribble from Friendly’s and, finally, a request for a date (after the pneumonia was gone, obviously.) 10 wonderful years later, the rest is history for these high school sweethearts!