* BigLippedAlligatorMoment: The sequence with Nick dancing (albeit, drunkenly) to "I Won't Dance" by Frank Sinatra. However, the scene may also just be RuleOfCool because it is massively fun to watch him dance around with his CoolHat.
* CrowningMusicOfAwesome: Several FrankSinatra songs play during the film since Nick is a huge fan of the guy.
** As is director Nancy Meyers; Sinatra often appears in many of her films.
* HarsherInHindsight: Creator/MelGibson in a romantic comedy with Helen Hunt, a Jew. Think about it.
* SoBadItsGood: The movie's sexism is so ridiculous that some people can't help but laugh at it.
* TearJerker: Erin the File girl.
-->''(Thinking)'': "Oh, god! He almost killed me! ...Too bad he missed."