A romantic comedy written and directed by Amy Heckerling, starring Creator/MichellePfeiffer, Creator/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:

* AmicablyDivorced: Rosie and Nathan, more or less.
* AsHimself: Henry Winkler, who Izzy prank calls.
* BerserkButton: Jeannie gets Rosie ''really'' mad when she breaks the necklace Izzy made for her.
* BettyAndVeronica: Jeannie fancies herself as the Veronica to Rosie's Betty, with Adam as Archie. But Adam has no interest in Jeannie, going after Rosie from the start.
* BitchAlert: Jeannie establishes herself as the below trope in her first scene by being a GracefulLoser when Rosie gives her bad news, but then immediately saying nasty things about her once she's gone.
* BitchInSheepsClothing: Jeannie (or as [[{{Malaproper}} Izzie]] called her, "past aggressive").
* ButNotTooWhite: Taylor is incredibly over-tanned.
* CatFight: Rosie and Jeannie.
* CharacterTics: Rosie's voice going all high and squeaky when she's really mad.
* CoolestClubEver: Where Adam and Rosie go on their first date.
* CostumeTestMontage: Rosie does this for her first date with Adam.
* DeadpanSnarker: Rosie and Adam.
* DisproportionateRetribution: Jeannie tries to sabotage Rosie's relationship with Adam just because her scene was cut from an episode of Rosie's sitcom.
* DoubleEntendre: Nathan claims his ass is his best feature.
--> '''Rosie:''' You know what, you're right. That's what everyone says: 'there goes Nathan. What an ass.'
* EurekaMoment: Rosie has one where she finally realises that Jeannie has been manipulating her.
* FirstKiss: Take a wild guess. (Cue [[StandardSnippet Romeo and Juliet Love Theme]].)
* FunnyBackgroundEvent: Mother Nature's reactions to what Rosie is doing in a lot of her scenes.
* 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.
* HollywoodOld: Subverted. Rosie is forty but believably passes herself off as thirty seven to Adam. And in real life, Michelle Pfeiffer was seven years older than her character.
* IAmNotPretty: Izzie thinks this in one scene. It seems to run in the family, judging by how hard Rosie is on her own appearance.
--> "Things are falling down, ''everything'' is drying out. I am hurdling towards Cloris Leachman..."
* 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.
* MayDecemberRomance: Parodied. Rosie treats her relationship with Adam like it's this but it's shown how silly she's being. The age difference is his 29 to her 40.
* NoPeriodsPeriod: Averted where Izzie gets hers early on and excitedly shops for tampons with Rosie.
* OlderThanTheyLook: Nathan believes this, and Rosie advises everyone to say he looks 32 to spare his feelings. Rosie is a straight example - being 40 and passing for 37 initially. Her actress was ''47'' at the time. The movie parodies this with Stacey Dash and Paul Rudd playing 20-somethings who play teenagers on a sitcom.
* ParentWithNewParamour: Type 1.
* PetHomosexual: Taylor, the TV show's stylist.
* PlotParallel: Rosie & Adam and Izzie & Dylan
* PublicServiceAnnouncement: Brianna does an anti-smoking PSA, then immediately starts smoking.
* RelationshipSabotage: Jeannie tries to do this to Adam and Rosie.
* SadistTeacher: Appears to be the case with Izzy's math teacher, who fails her for not showing her work in the same way as everyone else - despite getting the questions right.
* 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.
* SidetrackedByTheAnalogy: Nathan tells Rosie to stay with Adam, saying he's trying to be Bruce Willis to Adam's Ashton Kutcher. They get sidetracked wondering how Demi Moore's name is meant to be pronounced.
* 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.
* TheTalk: Initiated by Izzy.
--> '''Izzy:''' When can I have sex?
--> '''Rosie:''' When you get your Masters Degree.
--> ''They haggle over the number. Izzy wants fifteen and Rosie insists seventeen.''
--> '''Izzy:''' But mom, fifteen is the new seventeen.
* TotallyRadical: Parodied by Rosie's attempts to write teenage slang for her show. One of her {{Establishing Character Moment}}s is asking her daughter if people still say "gee" anymore.
* UglyGuyHotWife: Well they're divorced now but it was still Jon Lovitz married to Michelle Pfeiffer.
* WiseBeyondTheirYears: Izzie, to an extent; though in many ways she's quite typical of her age.
* YourCheatingHeart: The network executive is married but sleeps with a lot of the women on staff. Jeannie tries to make Rosie think Adam is cheating on her with Brianna.