To lift Antonio's spirits after he's dumped by the "Big Faced Girl," Joe and Brian set him up with a girl at the Club Car only to discover later that she's a very expensive hooker.

Joe and Brian are thrilled at the return of Grandpa Hackett, but Helen isn't so sure he is who he claims to be. Meanwhile, Antonio refuses to continue a chain letter, which everyone else gets and passes along, and begins to suffer for it.

Antonio thinks his fortunes have taken a turn for the better when one of passengers hires him to be his personal chauffeur. But some overheard conversations seem to indicate that his new boss is a mobster.

Meanwhile, Helen hurriedly reads "Don Quixote" when her old English Literature teacher from high school drops by for a visit.

Joe faces a moral dilemma: can he lie to Helen so he can go to a strip club with Brian? To soothe his conscience, he volunteers some time at the Golden Crest retirement home, but ends up taking one of the residents with him to the strip club.

Meanwhile, Fay and Antonio write their own eulogies.

A financial crisis forces Joe to seek out an investor for Sandpiper. He thinks his luck has changed when businessman Jonathan Clayton comes to the island. But he soon informs them he doesn't invest in companies; he buys them.

Joe and Helen deal with a crooked vacuum cleaner salesman charging them to repair a vacuum originally sold with an "eternal" guarantee.

Meanwhile, Brian gets close to Roy to get closer to his niece.

On their way home from Las Vegas, Joe has a bad case of food poisoning and is soon helpless in the airliner's bathroom, where he is soon followed by the plane's pilots. This leaves the job of hero to be played by Brian, who safely lands the plane and becomes an instant celebrity.

Joe tries to deal with Brian's newfound celebrity and all the grief he's getting from Helen over his "Men's travel bag", but Brian's celebrity is short lived and he soon is back at Sandpiper asking for his old job back once again.

When a long time rival drops out of a boxing tournament, Joe finds himself matched up against Brian. But what starts out as a friendly competition gets decidedly unpleasant.