In the tradition of Boogie Nights, Secretary takes the taboo and wraps it in a typical romance format. Boogie Nights told a coming of age family story that happened to involve porn; Secretary tells a romance that happens to involve sadomasochism.
Our heroine is the vulnerable Lee Holloway (Maggie Gyllenhaal, sister to brother Jake of Donnie Darko fame). Gyllenhaal has a waifish, almost unearthly look about her that radiates a sad vulnerability, which makes her perfect for the role. As Lee, she players a character filled with self-loathing, hating herself so much that she not-so-secretly cuts her thigh with a razorblade. When her parents eventually discover her destructive habits, they commit her to a mental institution. Lee is eventually released, but she will never truly get "better."
As an important first step in escaping her restrictive home life, Lee gets a job as a secretary. She works for the intimidating Mr. Grey (James Spader), who brooks no failure. Working for the handsome boss turns out to be a challenge Lee enjoys, in more ways than one.
Once Mr. Grey discovers that Lee is a masochist, he takes slowl but subtle control of her world. Grey alternately sets Lee free and dominates her by telling her she will never cut herself again. And Lee complies, throwing away her box of sewing equipment that she used to mutilate herself.
But Lee's release is also a taste of the forbidden that she craves. Eventually, Mr. Grey resorts to spanking as a form of discipline, a torture she enjoys. Thus begins the S&M relationship between boss and secretary.
Although they don't sleep with each other, the two engage in kinkier pleasures as the days go by. In the mean time, Lee continues the façade of a normal life, dating a bland boy named Peter (Jeremy Davies) who offers an equally bland future. Eventually, he proposes; in a haze, Lee accepts.
But she shouldn't have, and she knows it. Mr. Grey's affections stop as he is overcome with guilt for what he has done to Lee. He fires her and, we come to realize, perpetuates a cycle of anticipation, secret pleasure, and guilt. But unlike the secretaries in the past, Lee has no intention of giving up on her man.
The ending is at least as torturous as the movie itself is to watch. Mr. Grey, disturbed at Lee's infatuation with him, orders her to sit at his desk and stay there until he says otherwise. Finally standing up for something, anything, Lee refuses to remove her palms from the desk. For days.
Secretary is a character piece, and Lee does not disappoint. She puts her considerably talents, her raw vulnerability, before the camera both physically and emotionally. She's so vulnerable, in fact, that it's sometimes hard to watch.
Despite its subject matter, Secretary steadfastly refuses to exploit its characters. Secretary lays the framework for a typical romance, despite the fact that it sometimes involves spanking and a horsewhip. We come to realize that these two deeply troubled people relate to each other through pain. And as long as they trust each other, that's okay.
Although it's certainly not for everybody, Secretary puts an entertaining twist on the usual boy meets girl format. It's more girl meets boy, boy spanks girl, and they live happily ever after.