Lee Holloway (Maggie Gyllenhaal) has a few strikes against her when she applies for a secretarial position at the law office of E. Edward Grey (James Spader). For starters, she was released only recently from a mental institution. However, she gets the job anyway and soon learns that Mr. Grey is not your average boss. Eventually, they begin a relationship, crossing lines of conduct that would give most human resource directors the shivers.