Lee Holloway (Maggie Gyllenhaal) just got out of a mental institution for cutting her self due to stress, and now comes home to even more stress including her overprotective mother (Leslie Anne Warren) and resorts back to her old habits. She soon decides to get a job in typing and instantly becomes skilled, looking for a job. She stumbles upon a small law firm run by a militant E. Edward Grey (James Spader) who is mostly professional and soon develops an odd fascination with her. They soon find they each have a fancy for the sadomasochistic. The aspect that makes this movie so unique is that both characters are so pathetic at times, and somehow become drawn to each other. Grey is a lawyer in a quiet and boring firm who quivers in his office, and Holloway is a nimble and meek girl who tends to hide behind her desk; self inflicted torture is what draws them together emotionally and sexually.

