I Could Never Be Your Woman

A romantic comedy written and directed by Amy Heckerling, starring Michelle Pfeiffer, Paul Rudd, and Saoirse Ronan. 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 Executive Meddling 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:

 * Actor Allusion: Paul Rudd and Stacey Dash play adult actors who play teenagers in You Go Girl!, referencing their both previously having been in Clueless, which was, like this movie, written and directed by Amy Heckerling.
 * Amicably Divorced: Rosie and Nathan, more or less.
 * As Himself: Henry Winkler
 * Bitch in Sheep's Clothing: Jeannie (or as Izzie called her, "past aggressive").
 * Cat Fight: Rosie and Jeannie.
 * Coolest Club Ever: Where Adam and Rosie go on their first date.
 * Costume Test Montage: Rosie does this for her first date with Adam.
 * Dawson Casting: Parodied
 * Deadpan Snarker: Rosie and Adam.
 * Fake Nationality: Aside from Ronan, there are several other Irish and British actors in the film.
 * First Kiss: Take a wild guess. (Cue Romeo and Juliet Love Theme.)
 * Green Aesop: Downplayed for laughs. Mother Nature 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.
 * I Am Not Pretty: Izzie thinks this in one scene.
 * Inner Monologue: Rosie occasionally argues with her own subconscious, which takes the form of Mother Nature (though Mother Nature also appears to serve a bit of a Narrator role for the film, independent of Rosie).
 * Little Miss Snarker: Izzie
 * Makeover Montage: A slight example is done for Adam's character on the show.
 * Parent with New Paramour: Type 1.
 * Plot Parallel: Rosie & Adam and Izzie & Dylan
 * Public Service Announcement: Brianna does an anti-smoking PSA, then immediately starts smoking.
 * Shout-Out: The Graduate; Adam jokingly calls Rosie "Mrs. Robinson" 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.
 * Song Parody: Izzie does this to songs by Britney Spears and Alanis Morissette.
 * Spit Take: Played straight by Mother Nature in one scene. Played for Laughs (if that's not too redundant) by Adam in a later scene.
 * Terrible Interviewees Montage: Adam is the only good actor to audition for a role on the show; his audition might be considered a Meet Cute for him and Rosie.
 * Totally Radical: Parodied by Rosie's attempts to write teenage slang for her show.
 * Wise Beyond Their Years: Izzie, to an extent; though in many ways she's quite typical of her age.
 * Write What You Know: 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.