Alex Sheldon (Wilson) is a popular author of romantic comedy novels. The two novels he's written have touched the populace with their mix of humor and heartwarming moments. Unfortunately, Alex has a penchant for gambling, and has a debt of one hundred thousand dollars to the Cuban mafia. After breaking into his apartment, destroying his computer, and dangling him out a window, the mobsters give him an ultimatum: pay the money in one month, or die. Alex can't get any more advances from his publisher, which means that he has to write another bestselling novel in just thirty days.
With no computer, he has to get a stenographer. After misrepresenting himself as a legal firm to hire Emma Dinsmore (Hudson), he barely convinces her to stay. Thus the writing begins.
This film contains examples of:
- Betty and Veronica: In Alex's novel, Polina (the Veronica) and Anna (the Betty). Later, Polina (Veronica) and Emma (Betty)
- Blonde, Brunette, Redhead: The three different au pairs in Alex's novel, who are Emma's equivalents: the character starts as the Swedish and blonde Ylva, then the German and redhead Elsa, and finally the American and brunette Anna. The brief Spanish au pair before Anna, Eldora, was also a brunette.
- Composite Character: Alex says that his character Polina is this for several women he knew throughout his life. Not entirely so...
- "Friends" Rent Control: In the words of Roger Ebert, "All Alex has to do is sublet, and his financial worries are over."
- I "Uh" You, Too: Trope Namer. Happens between Alex and Emma near the end.
- Most Writers Are Writers: The protagonist writes novels.
- Name and Name
- Show Within a Show: Scenes from Alex's novel make up half the film. The characters are (mostly) played by their equivalents in the "real world". Including the dancing mafiosos.
- It's interesting to note that Emma's equivalent in the world of the novel change as Alex's views of her change. This annoys her to no end, as she's the one who has to retype the whole thing every time.
- The Roaring '20s: The time period of Alex's novel
- Write What You Know: Alex bases the characters off the people he knew and knows in real-life
- Very Loosely Based on a True Story: The working title was actually Loosely Based on a True Love Story, due to being based on basically the same thing happening to Fyodor Dostoevsky.