Joe and Helen hire an architect to build their dream house.

Brian's incessant eating affects his work; Joe tells him to get his act together. Helen tells Brian he should attend her overeaters support group meetings; when Brian goes, he reveals why he is eating so much. Antonio buys a pair of expensive shoes that are a little tight; he says he just has to break them in, but it appears his feet will break first. Casey goes to a job interview and pretends to be a fan of the Three Stooges because the interviewer is a Three Stooges fan.

Helen and Joe argue over details of their new house. Antonio takes his new self-help tapes to an extreme, and Casey's horrible new Nantucket Island slogan all work their way into Joe's dreams.

It's Christmas. Joe wants to go on a last-minute Vermont ski trip with Helen, but she wants to throw her planned traditional Christmas party. Joe agrees on the condition they leave for Vermont as soon as the party is over. Brian tells Casey he's bringing a date, informing her because of their relationship. She tells him she's also bringing a date. She later lies, claiming the repulsive Lewis is her date. During the party, Joe learns that snow will shut down travel to Vermont, so he tries to rush the party. Antonio brings gifts for everyone, but they don't reciprocate so he gets irate. When everybody tries to leave, Helen stops them. The partygoers soon discover their wallets are missing, and they accuse each other.

Casey brings a TV star to Nantucket to help publicize the island. Joe and Helen take care of their friend's child to see if they will make good parents.

Lyle, a man Fay met while on vacation comes to the island to court her. He proposes to her and they were in the process of getting married when the minister utters his full name. That's when Fay freaks out, because he has the same name as her other dead husbands. She then goes to Joe who is nursing a cold to ask him what she should do.

In the air on Valentine's Day, Brian and a passenger fall madly in love with each other. On the ground, Roy has a date with Antonio's former girlfriend - Edna, the big-faced girl.

Antonio thinks his fortunes have taken a turn for the better, when one of his passengers hires him to a be his personal chauffeur. But some overheard conversations seem to indicate that his new boss is a mobster (he's actually a diamond broker). Meanwhile, Helen hurriedly reads "Don Quixote" when her old english lit teacher from highschool drops by for a visit.