While Alan and his friends prepare for their first high school dance, Nathaniel asks questions about dating and George and Phyllis make arrangements to go to Ben Maksik's Town and Country Club. The night of the dance Sid plans to take out a girl named Flora in a gorgeous brand-new 1957 Edsel borrowed from his sister's husband, but unfortunately neither Flora or Benny's date, Becky Abromowitz, show up, leaving the two to discuss life and love while waiting at the store. Meanwhile, Grandma and Grandma make a "date" to play cards with Nathaniel.

Phyllis invites an old school friend and her husband to a dinner party at the Silvers', but as the night progresses she and George are left uncomfortable by their constant bickering, while Grandma disapproves because the rest of the family wasn't invited to join them. In the meantime, Nathaniel mourns the loss of The Buccaneers, a favorite Saturday night program that's been replaced by Perry Mason.

George is upset when his sister Alice arrives for a visit to discuss selling his parents' bungalow at Mountaindale in the Catskills, remembering the good times the family has always had there and fearing they are losing part of their heritage; in the meantime, Phyllis is offered a promotion--but at the expense of Emma Brooks, the office manager who's been her mentor.