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It is a story about Lee, an emotionally unstable woman (Maggie Gyllenhaal) who starts the film after being released from a psychiatric hospital, where she was put after an incident of self-harm went too far. She finds a job as a typist under Edward, a demanding lawyer (James Spader). After some time, the two develop a sadomasochistic relationship, and are forced to deal with the personal and professional consequences.
Based on a short story by Mary Gaitskill, who is known for stories centered on emotionally damaged women and deviant sexuality, and directed by Steven Shainberg. Also notable for some unusual choices in direction, particularly with regards to soundtrack; the development of the relationship between the main characters is marked by the length and quality of the silence between them.
- Adaptation Expansion - The original story is only 15 pages, and the protagonist is not named.
- The Alcoholic: Lee's father.
- BDSM Equals Love: The film doesn't really show Lee and Grey share anything other than their fetishes... unless you count the mutual inability to open up emotionally, a very deep shyness that they handle in different ways. A longing to really understand each other, without really daring to let it go anywhere.
- Bondage Is Bad: Edward seems to have this mindset in the beginning, giving him some internal conflict.
- Casual Kink: While most of Secretary averts this trope quite hard, it does pop up twice. In the middle of the movie, Lee is listening to a tape about coming out as a dominant or submissive, assuring the listener that BDSM is a capacity for a wider range of experience. More importantly, the movie has a happy ending where Lee finally gets rid of her fiancée (whom she never wanted, he was pushed on her and she wasn't assertive enough to say no), come out as a masochist and finally demand a real relationship with Edward. Some people are pissed at her, but her father stands by her side and asserts that he's proud of her. Edward overcomes his fear and they live happily ever after.
- Conveniently-Common Kink: Inverted. Lee only discovers her fetish during her stint as the secretary, so Grey directly influences her "choice" of kink.
- Extreme Doormat: At the beginning of the film, Lee is such a doormat that she can't even hang up on a telemarketer. Becoming a BDSM submissive makes her more assertive.
- Happiness in Slavery
- Hollywood Masochism: Averted except for the basic premise: Being one of the very few romantic comedies about BDSM, it is also the perhaps only romantic comedy that starts with the protagonist getting out of a mental hospital (and she didn't end up there out of some wacky misunderstanding).
- Internalized Categorism: At first, Edward believes that bondage is bad. It makes him very unfair to himself and his submissive, who he seems to blame for tempting him. Lee eventually manages to snap him out of it.
- Pitying Perversion: Secretary is one of the very very few romantic comedies with a masochist as the protagonist. It is also the perhaps only romantic comedy that starts with the protagonist getting signed out from a mental hospital and has a lot of heavy mental problems that are not Played for Laughs at all. Also, when she tries to date around to find a new partner to satisfy her masochism, all the partners that she encounters are unsuitable.
- Property of Love: The kind of relationship Lee wants, and gets in the end. The film is a mixture between drama and Romantic Comedy, revolving around the BDSM version of this trope. The main storyline is about the main character wanting to be truly owned by her boss.
- Revised Ending - The original story ended with the protagonist quitting, feeling disgusted, and then being called by a reporter digging for dirt after "the lawyer" announced he was running for mayor. The movie ends on a much happier note.
- Safe, Sane, and Consensual
- Sexy Secretary
- Shrinking Violet: Lee
- Spank the Cutie: Lee Holloway's boss, Mr. Grey, originally spanking Lee for typos.
- The Stoic: Edward
- Truth in Television: See Extreme Doormat above. Anecdotally, there is nothing ironic about it at all. Many people who have submissive desires find themselves empowered when they are able to experience those desires with a caring partner. Further, Lee acting as the strong emotional center and her strength being what allows the dominant to embrace his role in their relationship is also quite common. It's called power exchange for a reason.
- You Make Me Sic: Mr. Grey's displeasure with Lee's spelling errors and typos are an entry into kinky sex.