Gregory's Girl is about Gregory (John Gordon Sinclair), a young high school boy who is discovering the ways of the opposite sex. Gregory is a rather daft, clumsy boy who plays soccer on a losing for the school team. The coach decides new talent is needed so tryouts are held. A girl Dorothy (Dee Hepburn) tries out for the team. She proves to be very skilled and scores in her first game with the team. Gregory falls for Dee. To help him get achieve his aim of getting a date with Dee, his precocious young sister Madeleine who advises him. While Gregory is chasing after Dee, he is being eyed by Dee's friend Susan (Clare Grogan) who takes her own interest in Gregory. Eventually, at practice Gregory has the courage to ask Dee out for a date. Who is going to end up being Gregory's Girl?