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.

----
!!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.
* 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.
* 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 twenty nine to her forty.
* NoPeriodsPeriod: Averted where Izzie gets hers early on and excitedly shops for tampons with Rosie.
* 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.
* 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.