Lee Holloway (Gyllenhaal) has a few strikes against her when she applies for a secretarial position at the law office of E. Edward Grey (Spader). First, she was released only recently from a mental institution; second, after only one day back with her dysfunctional suburban family, she has already succumbed to her secret, self-destructive habit. Although she's never had a job in her life, Lee is hired by the mysterious lawyer, Mr. Grey. At first the work seems quite normal but soon, in between typing, filing and coffee-making, Lee and Mr. Grey embark on a more personal relationship altogether, crossing lines of conduct that would give any human resource director the vapors.