The Many Loves of Dobie Gillis

Dobie is desperate for money so he can take Thalia to the dance, so he and Maynard hatch a plot to dishonestly win $100 at the Bijou Theater on Jackpot Night.

Dobie launches a runway offensive versus wealthy, better-dressed hunk Milton Armitage, his competitor for luscious teen gold-digger Thalia Menninger. When Dobie's grocer father refuses to finance a clothing binge, Dobie talks a local haberdasher into letting Dobie secretly model the shoppe's best outfits, to promote the store's business.

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. Pomfritt and Dobie host a testimonial farewell dinner for him. This episode introduces Michael J. Pollard as Maynard's beatnik cousin Jerome.

When Dobie starts singing like Elvis Presley, he finds that it drives the girls at school wild. What's even better is that Thalia Meninger, the love of his life, has taken notice and decided to become his manager.