 Sammy, is an awkward, unhappy College freshman. He s madly in love with the beautiful but unapproachable Pauline. Sammy s luck seems to change when he meets a mysterious man, who appears to have walked right out of the 1940 s and straight into Sammy s modern angst. Raleigh is smooth and worldly-wise. He tells Sammy everything he needs to know to get the girl. But what Sammy doesn t know is that Raleigh has plans of his own for both Sammy and the object of his affection.