Secretary is a 2002 independent film directed by Steven Shainberg and starring Maggie Gyllenhaal as Lee Holloway and James Spader as E. Edward Grey. The film is based on a short story from Bad Behavior by Mary Gaitskill, and explores the relationship between a sexually dominant man and his submissive secretary.
Lee Holloway (Maggie Gyllenhaal), the socially awkward and emotionally sensitive youngest daughter of a dysfunctional family, adjusts 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, E. Edward Grey (James Spader), who hires her despite her stilted social skills and unprofessional appearance.
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 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 normal 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 eagerly complies. Days pass, as Peter, family members, and acquaintances individually visit Lee to alternately attempt to dissuade or encourage her. After three days, Edward returns to the office and takes Lee to his apartment where he bathes and nurtures her. The pair marry and happily continue their dominant-submissive relationship.
- James Spader as E. Edward Grey, Lee's employer and sexually dominant lover
- Maggie Gyllenhaal as Lee Holloway, the eponymous submissive secretary
- Jeremy Davies as Peter
- Lesley Ann Warren as Joan Holloway
- Stephen McHattie as Burt Holloway
- Jessica Tuck as Tricia O'Connor
- Oz Perkins as Jonathan
- Amy Locane as Lee's sister
- Patrick Bauchau as Dr. Twardon