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A Romantic Comedy farce that lampoons romantic comedies around the 1950s and early 1960s, particularly the Rock Hudson and Doris Day films.
Author Barbara Novak (Renée Zellweger) arrives in New York to publish her book, Down With Love. It becomes an international best seller, even edging out a biography of John F. Kennedy, and millions of women buy it and start learning from its precepts. This does not sit well with the majority of males in the world, least of all Catcher Block (Ewan McGregor), a reporter for Know Magazine, and a Casanova rivalling James Bond in both suaveness and libido. After Novak calls him out for his behavior on national television, he hatches a scheme to get her to fall in love with him, thereby violating the first of her rules, not to fall in love. She's already expressed her displeasure with him, so in order to get into her pants, he fabricates the persona of a country-boy astronaut who has just touched back down to earth, and as such has no idea of her book or her identity.
There is also a Beta Couple of Barbara's best friend Vikki Hiller and Catcher's neurotic boss Peter MacMannus, who get drawn into the hijinks of Catcher and Barbara.
This film shows examples of:
- All Men Are Perverts: The senior editors of Banner House lean forward eagerly as Barbara begins elaborating on the self-pleasuring technique outlined in her book...then sit back in disappointment when the chapter's title turns out to be "Up With Chocolate."
- All-Star Cast
- Becoming the Mask: Nancy becomes Barbara
- Beta Couple: Vikki and Peter.
- Big Applesauce
- Casanova: Catcher Block, so much.
- Does This Remind You of Anything?: Via the magic of Split Screen, Barbara and "Zip"'s conversation looks like a sex scene, complete with cool-down cigarette.
- There's also Catcher and Peter's conversation about the length of their... socks.
- Everything Is an iPod In The Future: Not The Future", but Now magazine's offices are built to be much more round than their competitor's.
- Feng Schwing: Spoofed with Catcher's apartment, which, among other things, has a hideaway bar that takes up the entire wall.
- Fridge Logic: Head on down to Tethercat Principle.
- Heroes Want Redheads
- Hey, It's That Guy!!: It's Niles!
- Hurricane of Puns: Catcher and Barbara's conversation near the end, about their two magazines, "Know" and "Now".
- I Know You Know I Know: How Nancy/Barbara knew her plan would work.
- Irony as She Is Cast: Vikki and Peter are played by two "out" actors. with many knowing in-jokes about Peter not being gay even though Vikki thinks he just might be.
- Although strictly speaking, neither of them were out publicly at the time of the movie's release, although in Hyde-Pierce's case it was something of an open secret.
- Ladykiller in Love
- Leaning on the Fourth Wall: At dinner, Vikki tells Peter how she dismissed the theory that life was a zany sex comedy in which he switched keys with the lead to ensnare her. Unsurprisingly, the theory that Peter was gay made more sense.
- Line-of-Sight Name: Catcher's alias of "Zip Martin", via signs in a drycleaning.
- Living Legend: Catcher Block, ladies' man, man's man, man about town is an in-universe Memetic Sex God.
- Mistaken for Gay: Peter, played by gay actor David Hyde-Pierce.
- The Mistress: The mistress of Theodore Banner, head of the publishing house, stops listening to him, thanks to the book.
- Offscreen Teleportation: Barbara appearing in the elevator at the very end, when Catcher had just tried to apologize to her in her office.
- Opera Gloves: A few of the dresses, including the gold dresses the triplets wore.
- Overly Narrow Superlative: "Oh, Vikki! You're the best friend a girl from Maine who wrote a book and came to New York could ever have!" Meant as a genuine compliment.
- Out-Gambitted: Novak pulls this on Block. It works out well for both of them though.
- Power Blonde: She's the cool, blond Barbara Novak.
- Pretty in Mink: Vikki wears a mink wrap for a date, and the triplets wear identical white fox wraps.
- Punny Name: Catcher Block
- Sexy Stewardess: Catcher Block seems to attract these like flies.
- Straw Feminist: Parodied; the female characters spend the movie bouncing wildly between the early 1960s version of this trope and it's 'Barbie doll housewife' extreme opposite.
- Triplet Threesome Fantasy
- Xanatos Roulette: Barbara/Nancy's entire plot to snare Catcher, which essentially hinges on her uncanny prediction of the entirety of the film's events up until the point of her revelation.