In this romantic comedy, good friends change their feelings about each other over the course of their four years in college. Ryan (Freddie Prinze Jr.) and Jennifer (Claire Forlani) have known each other since grade school, though their oil-and-water personalities don't always mesh. Engineering student Ryan focuses on his studies and future career, while Jennifer likes loud music, partying, and not doing her homework. As they suffer their share of disastrous relationships, these two opposites begin to wonder if they were meant to be more than friends. The supporting cast includes Jason Biggs as Ryan's loudmouth roommate Hunter, Amanda Detmer as Jennifer's neurotic pal Amy, Alyson Hannigan as Ryan's sometime girlfriend Betty, and Heather Donahue, who is no worse for wear after her experiences in the Maryland woods in The Blair Witch Project. Director Robert Iscove also worked with Prinze on She's All That (1999).
by Mark Deming synopsis