Secretary (2002)

Lee is portrayed at the outset as the 'crazy' one, just getting out of an institution and all the stuff she does at her sister's wedding. But, in very short order we are shown that she's at most one of many. Her family is a bit, um, shall we say, functionally fucked up. She's really just a confused young woman.
E. Edward Gray, Attorney at Law, appears to be the opposite of Lee. He's confident, well-dressed, knows what he wants. But, really he's just as confused as she is. It just takes him longer to figure it out.
It's not until after they both figure out what is up with themselves, i.e. that they don't know what is up, that they can leave the confusion behind. It's really a very touching story, and I'm not one who normally goes in for a romantic film.
I adore Maggie Gyllenhall. She is so sweet and vulnerable as Lee Halloway. One of the barometer's I use for how good of a job an actor is doing, and how good the film is as well, is how long before I forget I'm watching so-and-so and just see the character. It's not the only thing I use, there are some actors that I can never forget who they are, but like their films just the same, like John Cusack. But, in Secretary, by the time Lee has fled the wedding and gone upstairs into her room and taken out her little kit, I only saw Lee. This was such an intimate role, I don't imagine most actresses would ever even consider a taking a role where they are not wearing make-up and flattering clothes.
James Spader was an interesting choice, and no, I never forgot he was James Spader playing Mr. Gray, but that' alright. I thought I didn't like Spader. I know I certainly disliked films he did in the 80's, films that made me dislike Demi Moore and one ore more actors named Judd something-or-other. Because of this I probably missed out on some great legal dramas. He was okay in this film. I believed his character, and that's enough to kind of put aside the James-Spaderness of James Spader.

Secretary at IMDb