Annie (Neuwirth) works as a graphic designer at a fashion magazine. She's married to Tom, a lawyer, and they have two kids. Annie's life is getting stale, as she's hitting a mid-life crisis right after her 40th birthday, frustrated with a marriage that seems to be hitting the doldrums and life expectations unfulfilled. One day at work a disagreement with her boss blows up rather suddenly into an argument that gets Annie fired. Left rather stunned on the streets of New York after she leaves the building, she sees a place advertising golf lessons over lunch and enters on a whim. There she meets Fritz, a genial mall security head. She goes to Fritz's work and has an unexpected run-in with Christie, her old college roommate, who has an odd hobby.
Dear Diary was originally the pilot for an ABC sitcom starring Neuwirth. When it was rejected by the network it was shown in theaters as a short film, and it wound up winning the Academy Award for Best Live Action Short Film. It was an early DreamWorks production and was the first Dreamworks film to win an Oscar.
Not to be confused with the webcomic Dear Diary.
- Big Breast Pride: According to Annie, Madonna has this."She's very proud of her chest."
- Book-Ends: There's Annie scribbing in her diary at the beginning and the end, as well as having bad sex with Tom at the start (they give up) and good sex at the end after he sees her in the Little Black Dress.
- Buxom Is Better: Annie's editor Griffin accuses her of this, saying "What is it with you and breasts?" when seeing the proposed Madonna cover.
- Celebrity Paradox: Annie gets fired over an argument about the Madonna cover on that month's magazine. Havilland Morris, who plays Christie in this short, starred as Wendy in 1987 Madonna film Who's That Girl.
- Contrived Coincidence: In a city of eight million people or so Annie runs into her old college roommate, Christie, in a store. And Christie, as it happens, knows Annie's boss Griffin.
- Diary: The hook has Annie deciding to start keeping a diary now that she's turned 40. Presumably if the show had been picked up Annie's narration would have been in every episode.
- Dutch Angle: Used a lot, throughout the short, maybe to signal Annie's rather stressed life.
- Hollywood Midlife Crisis: Annie is having one, bored with her domestic life, imagining the career she could have had as a photographer.
- Imagine Spot: Many, like when Annie imagines being hit by a truck and killed, or when Tom imagines his dream career as the owner of a trendy restaurant.
- Little Black Dress: Annie uses these exact words when spotting said dress in the fashion store. She's surprised when Christie steals it.
- Rom Com Job: Lawyer? Graphic designer at a fashion magazine?
- Sports Widow: Fritz's wife is sick unto death of his obsession with golf, calling it "a disease".
- Stock Footage: Used several times to illustrate Annie's stories, like when she imagines being a photographer in Africa.
- Wardrobe Malfunction: Annie takes a good hard swing at a golf ball, causing her buttons to pop off her shirt and expose her bra, which all the men at the golf shop enjoy.