Dobie lies about joining the navy to impress a girl's sea-minded father.
Dobie meets Gwyneth, a simple girl who despises money, until her kid sister begins dating 13-year-old Chrissie Tyler, who runs a lucrative babysitting racket out of Charlie Wong's ice cream parlor.
Dobie acts impulsively and proposes marriage to Zelda.
After getting into a bit with a disgruntled police officer over picking flowers in the park Dobie goes to visit his new date that just so happens to be the officer's daughter.
Dobie falls for a nurse and fakes having a serious illness to win her attentions, but the disease he and Maynard plucked from a medical book sparks a panic.
Maynard is smitten with Francoise, and to compete with the similarly smitten Chatsworth Maynard trades in his sweatshirt and jazz sides for a sport coat and tie, but will he agree to shave off his beatnik beard?
When the Quimbys come to town and open a grocery store, Dobie competes with Chatsworth for Delphine's affections while Mr. Gillis competes with Mr. Quimby for the local grocery trade.
Dobie and Chatsworth compete for the affections of Daphne by setting to work to sell the most shoes in her father's shoe store.
Mr. Gillis dreads signing his will and suffers a nightmare of what his wife and sons would do with his store in his absence.
Chatsworth Osborne, Jr. agrees to assist the under-dressed Dobie and Maynard gain entry to his cousin Sabrina Armitage's black-tie soirée by having each fellow take a turn wearing his tux.
Thalia hatches a scheme for Dobie to sell sandwiches at the school picnic.
Dobie and Maynard strike out on their own and rent an apartment.
To help his father's chances of securing a loan, Dobie agrees to date the banker's spoiled-brat daughter.
Mr & Mrs. Gillis are persuaded to help with the Central High Student-Parent Betterment League's Capers, an amateur revue featuring acts of questionable talent.
Seeing a financial opportunity, Thalia gets Dobie and his Dad mixed up with a shady dry cleaning operation. Will she clean up while they're hung out to dry?
Dobie and a girlfriend take a baby-sitting job, but the Gillises suspect Dobie is secretly a father.
In Season One, we meet Dobie Gillis (Dwayne Hickman), who is obsessed with impressing and winning over the girl of his dreams, the beautiful Thalia Menninger (Tuesday Weld).
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