Mr. Grey has Lee bend over the desk and read a letter. While she is bent over, the lawyer slaps her hard on her buttocks. This little corporal ''encouragement'' is intended to bring out the best in Miss Holloway.  Lee Holloway (Maggie Gyllenhaal) is an unbalanced woman who returns to her Florida hometown following a brief stay in a mental hospital. She gets a job as a secretary in a law firm and develops an crush on boss, Mr. Grey (James Spader), a neurotic perfectionist. As their relationship moves toward the weird and weirder Lee follows her longings for masochism and finally to true love.