Our heroes Dobie Gillis (Dwayne Hickman) and Maynard G. Krebs (Bob Denver) are drafted into the army upon graduating from high school! But that doesn't stop Dobie from pursuing the girl of his dreams in fact, ANY girl. Any girl, that is, except the nagging, pestering Zelda (Sheila James), who continues to go to any length to prove that she and Dobie are meant for each other, including helping him write a song to win another teen's heart! Meanwhile, Dobie's new rich and snobby rival, Chatsworth Osborne, Jr. (Steve Franken) constantly interferes with Dobie's conquests by luring the young ladies away with money and expensive gifts. Guest stars include John Banner, Norman Fell, Jo Anne Worley, and Yvonne Craig.