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.
I was blown away by the writing, the acting, the depth and the sheer beauty of this film. A tale about youth, friendship and love, very sweet and tender, bitter and tragic at the same time. Also funny as hell, sometimes painfully so. Watching this film is like reading a very good novel. An unrecognized masterpiece. The ending is a little cheap though which costs it one star.