Linda's sister Gayle joins the family ski trip. But before she does so, she picks up a heavily medicated Bob from Dr. Yap, the family dentist. When Bob mistakes Gayle for Linda and kisses her, Gayle falls for Bob. So Bob turns to Dr. Yap for help.
The Belcher kids break their Halloween tradition by ditching their usual trick-or-treating route and venturing off to Kingshead Island, a posh neighborhood that is known for distributing full-sized candy bars. Meanwhile, Bob and Linda attend Teddy's annual "Black and Orange" party.
Bob worries he's depriving his children of their summer vacation by making them work at the restaurant, so he fires them. However, the kids become so bored with their newfound freedom that they secretly get hired by a pair of married hippie farmers, who hire the Belcher kids as "weed pickers." Meanwhile, Bob hires Mickey the bank robber to help out at the restaurant, but soon regrets his decision.