Young Lee Holloway (Maggie Gyllenhaal) has just been sent home to her parents after being hospitalized in a mental institution. She is a self-mutilator and can’t resist cutting herself whenever she is under stress. Her parents convince her to get a job and she begins working as a secretary for a lawyer, Edward Grey (James Spader). She begins dating an old school friend (Jeremy Davies) but can’t get over her dull depressive life. When Grey notices Lee’s cut marks he demands she never cut again. This demanding begins a strange sadomasochist relationship between Grey and Lee. As she no longer cuts she yearns for the approval of Grey and welcomes the inevitable spankings whenever she is bad. But how long can this relationship last before something goes amiss?