This is one of the craziest love stories you'll ever see. I guess many boss/secretary relationships are sadomasochistic, but no other film has ever made that so literal.
Lee Holloway (Maggie Gyllenhaal, DONNIE DARKO) has recently been released from a mental institution because she likes to cut herself. Her family is neurotic to say the least. Her father (Stephen McHattie, BASEKETBALL) is an alcoholic and her mother (Lesley Ann Warren, TWIN FALLS IDAHO) is an overly pleasant smotherer. Lee goes to an interview at the law office of E. Edward Grey (James Spader, SEX, LIES & VIDEOTAPE), a man who goes through so many secretaries that he has an illuminated "secretary wanted" sign outside the building.
His bag of narcosis is probably bigger than all the characters -- combined. He's domineering, sadistic, narcissistic and obsessive compulsive. Before long Lee and Mr. Grey strike up a sadomasochistic relationship where he spanks her for typing errors. Lee also has a relationship with a sensitive man her own age named Peter (Jeremy Davies, SAVING PRIVATE RYAN), but he doesn't meet her needs like Mr. Grey does and he'll never understand her as easily as Mr. Grey does either.
Director Steven Shainberg (HIT ME) has made his first film of note with this quirky romance that perfectly balances between drama and ironic comedy. The film subtly (maybe unconsciously) skewers all preconceived stereotypes about the relationships between secretaries and their bosses. And I guess the film does the same with romance. We always think that love is pretty and soft, but not for these characters.
One of the film's missteps is an event of "media coverage" at the tail end of the film. At first I thought it was a dream in Lee's head, but it's not and the action is rushed through and too much of a tone shift from the rest of the film.
Gyllenhaal delivers a strong performance that never seems silly or reaching for laughs. Spader is not a stranger to sexually provocative roles and his character was the most interesting to me because there was a buried repulsion to his behavior that he's developed that has left him emotional stunted.
If you look closer, the strangeness of their relationship is just window dressing. Like any great love story, the characters fall in love because they fulfill needs in each other that have never been met before. The only difference is that Lee likes things a little rough and Mr. Grey has finally found a secretary who understands his obsession with typos.