James Yagi

In order to obtain enough money to impress Thalia on their prom date, Dobie conspires with his beatnik friend Maynard to rig a raffle at the local movie theater.

Dobie tries to impress Thalia by dressing as nicely as the rich Milton Armitage. A frustrated Milton doesn't know that Dobie is borrowing his duds from a local tailor.

Thalia urges Dobie to become a doctor, but he meets Zelda Gilroy and learns about the scientific concept of propinquity, the psychological tendency for people to form relationships with those whom they encounter often.

Dobie's rarely seen older brother advises him to try to gain sympathy from a new girl in school by bemoaning his affair with a married older woman, but this causes the girl to conclude that Dobie is involved with their math teacher, Mrs. Adams.

In order to win Thalia from Chatsworth Osborne Jr., Dobie reads a book on mental power so he can be the dominating man that Thalia wants.

Thalia talks Dobie's parents into sending him to Willoughby, a local prep school. He doesn't attend, but Mr. Gillis has a dream in which he imagines Dobie with a rich roommate.