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Maggie Gyllenhaal stars in this off-beat comedy that looks at the world of sado-masochism. Lee Holloway (Gyllenhaal) has recently left a mental institute and has been released into the care of her over-bearing mother and alcoholic father. Determined to get her life together, she gets a job as a secretary for an attorney she does her best to please. But when her new boss, E. Edward Grey (James Spader), finds fault with her typing and begins to administer a rather unconventional kind of punishment (he spanks her), Lee realises that she quite enjoys it. However, Grey sacks her because he can't enjoy humiliating her when he knows she secretly likes it. But Lee has now developed a taste for it and will try anything to get back as Grey's secretary.