I Could Never Be Your Woman (2007)

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Rosie (40), a divorced mother, produces the has-been TV comedy You Go Girl. Her boss no longer allows the show to tackle any vaguely controversial subjects, so it seems doomed. Then she meets at an audition Adam Perl (29), an attractive, spontaneously funny, single actor. She successfully casts him, which revives the show's ratings. She also dates him, but her pathological insecurity, focused on their age difference, compromises the relationship. That culminates when she suspects him of infidelity with the show's star, and the studio gives those two their own sitcom.
Michelle Pfeiffer as Rosie
Paul Rudd as Adam
Saoirse Ronan as Izzie
Stacey Dash as Brianna
Fred Willard as Marty
Jon Lovitz
Sarah Alexander as Jeannie
Tracey Ullman as Mother Nature
Yasmin Paige as Melanie
Rory Copus as Dylan
O.T. Fagbenle as Sean
Jayden Berry-Garvey as Ike
Iddo Goldberg as Director
Noah Lee Margetts as Monty (as Noah Margetts)
Jonathan Ryland as Prop Guy
Full cast

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