Secretary (2002)

Lee Holloway is a smart, quirky woman in her twenties who returns to her hometown in Florida after a brief stay in a mental hospital. In search of relief from herself and her oppressive childhood environment, she starts to date a nerdy friend from high school and takes a job as a secretary in a local law firm, soon developing an obsessive crush on her older boss, Mr. Grey. Through their increasingly bizarre relationship, Lee follows her deepest longings to the heights of masochism and finally to a place of self-affirmation.