Catherine Hicks in Eight Days a Week (1997)

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Before Keri Russell was Felicity, the hottest girl in college, she played Erica, the hottest girl in town. Naturally, she has a jerk of a boyfriend, but that doesn't stop Peter (Josh Schaefer) from falling in love with her. Erica won't give Peter a chance at showing her his boyfriend skills, so he decides to camp out on her front lawn like he's waiting for Dokken tickets. Thanks for the advice, crazy Uncle Nonno! Good thing his pal Matt is there to keep Peter company and teach him how to get his sexual swerve on using fruit. When you watch the film, remember to hide the bananas.