Filmmaker Cullen Hoback travels to a private high school where he writes a script about a real couple and the student who comes between them.

A lighthearted story about a man and a woman who seem destined to be together... and the hilarious chain of accidents that seem determined to keep them apart!

Margaret keeps her neighbours at a distance and avoids contact except with Cara. She enjoys her company just for making music since Cara plays the violin accompanying Margaret at the piano. Because of her arthritis she accepts the housemaid Robin who wants to become an actress. With this naive pretty girl her life gets suddently really exciting and she makes a lot of new friends.

Paul Snider is a narcissistic, small time hustler who fancies himself a ladies man. His life changes when he meets Dorothy Stratten working behind the counter of a Dairy Queen. Under his guidance Dorothy grows to fame as a Playboy Playmate. But when Dorothy begins pursuing an acting career, the jealous Paul finds himself elbowed out of the picture by more famous men.

A semi-fictional account of how writer F. Scott Fitzgerald met his wife while he was in the army and stationed in Alabama in 1919.