Shoulda. Coulda. Woulda.
A successful author is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.
RatingsNo TellyFlick ratings yet
4.8/10Rating on TMDBFrom The Movie Database59 votes
Winona RyderScarlet Smith
Mark PolishHenry McCarthy
Sean AstinBig Girl
Hilary DuffShasta O'Neil
Josh HollowayWino
Jon CryerJavier
Chevy ChasePrincipal Marshall
Jessica St. ClairDarcy Portola
Frances ConroyMrs. Leuchtenberger
Marc BlucasBrad Nelson
Joanna CassidyMrs. Smith
Dee WallaceMrs. McCarthy
Michael GrossMr. McCarthy
Ken JohnsonMr. O'NeilJessica SchatzMrs. O'Neil
