The Many Loves of Dobie Gillis (1959)

Dobie Gillis is an average teenager living in average Central City with an average desire--girls! He lusts after many nubile women, notably Thalia Menninger. Rivals for affection include rich playboys Milton Armitage and Chatsworth Osborne, Jr. Dobie is fortunate to have loyal friends--beatnik Maynard G. Krebs and super-intelligent Zelda Gilroy, who knows Dobie is meant for herself one day.