The Many Loves of Dobie Gillis (1959)

Sensitive teenager Dobie Gillis exasperates his grocer father Herbert T. Gillis and is the apple of his mother Winnie Gillis' eye. Dobie has an almost singular focus on the opposite sex, more often than not the object of his affection being the beautiful but money hungry Thalia Menninger, who in turn often loves Dobie but always loves money more, which Dobie never has and in his current life direction probably will never have to the extent that would satisfy Thalia. If not Thalia, Dobie pursues several other girls in his search for true love. His best friend is Maynard G. Krebs, a largely clueless but kind-hearted beatnik and lover of jazz music, he who always does what his best buddy Dobie does, often much to the chagrin of others in Dobie's life. While Dobie chases girls, the one girl he knows he does not want but who in turn knows that one day she will become Mrs. Dobie Gillis is bright Zelda Gilroy, who largely uses logic to convince Dobie that she is the girl for him.