Taking his geeky prep school roommate, Jonathan Ogner (Andrew McCarthy), under his worldly wing, Skip Burroughs (Rob Lowe) packs him off to lose his virginity in Chicago -- where Jonathan unwittingly embarks on a torrid affair with Skip's mother (Jacqueline Bisset). But after learning that Jonathan isn't who he claims to be, she ends the liaison ... until Skip brings Jonathan home for Christmas. John Cusack co-stars in this rite-of-passage comedy.