When the Edgartown building inspector discovers that Leo is living above the bookstore, he threatens to fine George for violating a zoning ordinance. Leo convinces George to slip the inspector an envelope full of cash, which lands George in jail. George clumsily attempts to bribe a public official and lands in jail. When the Edgartown building inspector discovers that Leo is living above the bookstore, he threatens to fine George for violating a zoning ordinance. Leo convinces George to slip the inspector an envelope full of cash, which lands George in jail. Meanwhile, Casey and Ted don't know how to fire an incompetent waiter.

Secretive Sheila shows up one day in the bookstore, and George is somewhat stunned when she asks him out on a date. So is Leo, because he can't shake the nagging feeling that he and Sheila have met before. George's date is cut short when Leo finally remembers the shocking truth about Sheila and an old chapter in his life.