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.