An emotionally fragile woman recently released from a mental hospital for self mutilation goes to school to gain secretarial skills to gain employment. She has an alcoholic father and a co-dependent mother who are clueless as to who she really is which a tormented soul who really wants to find something with which she can find success. She is a great secretary and finds a job with a unique, old fashioned, but off center in charge boss with a somewhat sadistic sexual proclivity. She grows and evolves and so does he.
A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.
- Lee Holloway (Maggie Gyllenhaal), is a socially awkward and emotionally sensitive youngest daughter of a dysfunctional family. She has to adjust to normal life after having been hospitalized following an incident of dangerous self-harm. She learns to type, starts to date an acquaintance from high school named Peter, and begins to work as a secretary for an eccentric attorney, named E. Edward Grey (James Spader), who hires her despite her stilted social skills, unprofessional appearance and scoring higher than anyone he's ever interviewed therefore being really highly overqualified. Edward explains that it's dull work and they don't use computers, however Lee remarks that she is okay with these conditions.
Though at first Grey appears highly irritated by Lee's typos and other innocuous mistakes, it soon becomes apparent that he is sexually aroused by her submissive behavior. After he confronts her about her propensity for self-injury and commands that she never hurt herself again, the two embark on a BDSM (B&D (bondage and discipline) with S&M (sadomasochism or sadism and masochism) relationship. Lee experiences a sexual and personal awakening, and she falls deeply in love. Edward, however, displays insecurity concerning his feelings for Lee, and he shows shame and disgust over his sexual habits. After a sexual encounter in his office, he fires Lee.
During this period of exploration with Edward, Lee has also been attempting to have a more conventional boyfriend in Peter (Jeremy Davies), even engaging in lukewarm sex with him. After Lee is fired from her job, Peter proposes to Lee, who reluctantly agrees to marry him. However, while trying on her wedding gown she leaves and runs to Edward's office where she declares her love for him. Edward, still uncertain about their relationship, tests Lee by commanding her to sit in his chair without moving her hands or feet until he returns. Lee willingly complies. Hours pass, as Peter, family members, and acquaintances individually visit Lee to alternately attempt to dissuade or encourage her while Edward watches from afar, completely taken by Lee's compliance, and his resulting sexual arousal.
After three days, during which Lee has gained live news coverage in the media attention while on her, of what they've called "The Lee Holloway Hunger Strike", Edward returns to the office and takes Lee to his apartment where he bathes and nurtures her. At the end, Lee and Edward get married and happily continue their dominant-submissive relationship.