A romantic comedy written and directed by Amy Heckerling, starring Creator/MichellePfeiffer, PaulRudd, and SaoirseRonan. Rosie Hanson is a divorced woman in her 40s who writes and produces a teen sitcom. She becomes involved with a 29-year-old man named Adam Pearl, who is cast in a guest role on her show. While she worries about their age difference, as well as ExecutiveMeddling and possible cancellation, her daughter Izzie stresses over her first crush, on a boy named Dylan. Meanwhile, Rosie's secretary, Jeannie, tries to break up Rosie and Adam, by manufacturing evidence to suggest Adam is secretly seeing Brianna Minx, the star of Rosie's show.

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!!This film provides examples of the following tropes:

* ActorAllusion: Paul Rudd and Stacey Dash play adult actors who play teenagers in [[ShowWithinAShow You Go Girl!]], referencing their both previously having been in Film/{{Clueless}}, which was, like this movie, written and directed by Amy Heckerling.
* AmicablyDivorced: Rosie and Nathan, more or less.
* AsHimself: Henry Winkler
* BitchInSheepsClothing: Jeannie (or as [[{{Malaproper}} Izzie]] called her, "past aggressive").
* CatFight: Rosie and Jeannie.
* CoolestClubEver: Where Adam and Rosie go on their first date.
* CostumeTestMontage: Rosie does this for her first date with Adam.
* DawsonCasting: [[ParodiedTrope Parodied]]
* DeadpanSnarker: Rosie and Adam.
* FakeNationality: Aside from Ronan, there are several other Irish and British actors in the film.
* FirstKiss: Take a wild guess. (Cue [[StandardSnippet Romeo and Juliet Love Theme]].)
* GreenAesop: [[DownplayedTrope Downplayed]] [[PlayedForLaughs for laughs]]. MotherNature rants about the Baby Boomer generation disrupting the natural order of things (though some of what she says comes off as a bit sexist). But her main concern in this movie is not the environment, but people's refusal to accept their own aging.
* IAmNotPretty: Izzie thinks this in one scene.
* InnerMonologue: Rosie occasionally argues with her own subconscious, which takes the form of MotherNature (though Mother Nature also appears to serve a bit of a {{Narrator}} role for the film, independent of Rosie).
* LittleMissSnarker: Izzie
* MakeoverMontage: A slight example is done for Adam's character on the show.
* ParentWithNewParamour: Type 1.
* PlotParallel: Rosie & Adam and Izzie & Dylan
* PublicServiceAnnouncement: Brianna does an anti-smoking PSA, then immediately starts smoking.
* ShoutOut: TheGraduate; Adam jokingly calls Rosie "MrsRobinson" in one scene (he and Rosie quote lines from the movie as foreplay). In a later scene, Rosie and Mother Nature watch a scene from the movie.
* SongParody: Izzie does this to songs by BritneySpears and AlanisMorissette.
* SpitTake: Played straight by Mother Nature in one scene. PlayedForLaughs (if that's not too redundant) by Adam in a later scene.
* TerribleIntervieweesMontage: Adam is the only good actor to audition for a role on the show; his audition might be considered a MeetCute for him and Rosie.
* TotallyRadical: Parodied by Rosie's attempts to write teenage slang for her show.
* WiseBeyondTheirYears: Izzie, to an extent; though in many ways she's quite typical of her age.
* WriteWhatYouKnow: The plot was inspired by Heckerling's experience working on a show like the one Rosie writes in the movie, while raising a young daughter.