Uncle Bill agrees to let Sissy attend her friend Sutton's party until Mr. French discovers to his horror that it's an underwear-only get-together. Meanwhile, Jody and Buffy welcome the arrival of a new bunk bed complete with bells and whistles.

As Halloween nears, Uncle Bill and Mr. French plan a special trick-or-treat expedition when they realize that Halloween in New York City doesn't compare to the small-town holiday Buffy and Jody are used to. Meanwhile, Sutton tries to coerce Sissy into playing a Halloween prank on the building's superintendent.

When Uncle Bill forbids Sissy from going on her first date alone with one of her classmates, she devises a plan to get what she wants. Sissy learns a lesson though when her date doesn't go as smoothly as intended.