Judy tries to limit the time Bill spends with next-door neighbor Kyle Polsky (Todd Stashwick), whom she considers a bad influence, and calls him an "irresponsible man-child." However, she comes to regret those words after she forgets to mail Brian's college application and needs rich-alumnus Kyle's help getting him admitted.

Bill gets the little brother he never wanted when his father, Al (Paul Sorvino), visits and brings his perky new fiancée and her 9-year-old son, Billy, who seems to have become the apple of Al's eye---and proves to be an attention-grabbing thorn in Bill's side.