The Many Loves of Dobie Gillis

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.

Maynard receives his draft notice and Mr. Pomfitt and Dobie host a testimonial farewell dinner for him.

Dobie's popularity at school soars when a case of tonsillitis gives him a singing voice like Elvis Presley.