Lee Holloway (MAGGIE GYLLENHAAL) is a disturbed young woman who's been released from a mental institution and returns home on the day of her sister's wedding to live with their parents, Joan (LESLEY ANN WARREN) and Burt (STEPHEN McHATTIE). Needing a job to take her mind off her self-mutilation behavior, Lee applies for a secretarial position with E. Edward Grey (JAMES SPADER).
A mysterious lawyer who works in a building by himself and has had trouble retaining his previous secretaries, Edward hires Lee to type his paperwork. Yet, he doesn't allow her to use a computer and her typewriting results in several errors for which he instantly reprimands her.
Despite that, he also shows a certain compassion toward her, and his hot and cold behavior initially baffles and frustrates her. It eventually arouses her, however, and the two then ultimately enter into an informal and tentative S&M relationship that obviously puts a strain on her being engaged to Peter (JEREMY DAVIES), a former high school friend.
When Edward's sudden refusal to continue anymore causes Lee to question whether that's real or just part of his role playing, she must decide what she wants from him and for herself.