History Film / ICouldNeverBeYourWoman

* FirstKiss: Take a wild guess. (Cue [[StandardSnippet Romeo and Juliet Love Theme]].)

* IResembleThatRemark: Adam's indignant response told by Jeannie that his acting is too broad:

--> "Things are falling down, ''everything'' is drying out. I am hurdling towards Cloris Leachman..."

* 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.

* AsHimself: Henry Winkler, who Izzy prank calls.

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

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.

* UglyGuyHotWife: Well they're divorced now but it was still Jon Lovitz married to Michelle Pfeiffer.

* 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.

* IAmNotPretty: Izzie thinks this in one scene.

* 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.

* WiseBeyondTheirYears: Izzie, to an extent; though in many ways she's quite typical of her age.

* 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.

* AsHimself: Henry Winkler

* DawsonCasting: [[ParodiedTrope Parodied]]

* FakeNationality: Aside from Ronan, there are several other Irish and British actors in the film.

* 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.

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.

A romantic comedy written and directed by Amy Heckerling, starring Michelle Pfeiffer, 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.

* ActorAllusion: Paul Rudd and Stacey Dash play adult actors who play teenagers in [[ShowWithinAShow You Go Girl!]], referencing their both previously having been in {{Clueless}}, which was, like this movie, written and directed by Amy Heckerling.

* 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 [[YourMileageMayVary a bit sexist]]). But her main concern in this movie is not the environment, but people's refusal to accept their own aging.

* JerkAss: Jeannie

* ShoutOut: TheGraduate; Adam jokingly calls Rosie "MrsRobinson."