Pretty in Pink (movie, 1986)

Andie is an outcast, hanging out either with her older boss, who owns the record store where she works, or her quirky high school classmate Duckie, who has a crush on her. When one of the rich and popular kids at school, Blane, asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realize that dating someone from a different social sphere is not easy.