After struggling in New York for ten months and resorting to waiting tables at a strip joint, Helen relents and wishes to return to Nantucket. Joe and Brian bring her back, but Joe does not mention that he has a new girlfriend, Gail, even though he and Helen had already broken up. Helen reacts to the news by driving her Jeep Wrangler through Joe's office.
Joe sues Helen for running into his office. However, not even small-claims court can change Helen's anger. Tony Shalhoub joins the cast permanently as Antonio Scarpacci, former restaurant waiter who now is a cab driver.
Concerned by Helen's persistent anger over her break up with Joe, the rest of the group convince her to seek help with a transition group, not realizing exactly who the group is for. Meanwhile, after escorting Helen to the group meeting, Brian becomes obsessed with talking about Carol and takes over the group.
Lowell becomes paranoid, thinking that his wife Bunny (Laura Innes) is committing adultery. Lowell soon learns that paranoia does not nullify concern.
Roy's competition for the town council drops out, and the gang convinces Joe to run against him with Fay as a campaign manager. But when the local newspaper endorses Fay herself, Roy gets more competition than he can handle.
The arrival of Millionaire Mimsy Borogroves has Fay, Roy and Helen eager to tap into her wealth. But Mimsy has eyes for Brian, and he soon enjoys the good life, receiving expensive presents and accompanying Mimsy everywhere, much to Joe's disgust.
As his birthday approaches, Joe firmly insists that the rest of the gang not throw him a party. When Fay asks him to stay late to wait for a shipment of airplane seats, Joe becomes convinced they're throwing him a party anyway.
Joe doesn't like it when Helen becomes friends with his new girlfriend Gail. In a subplot, Roy tries to sneak aboard Air Force One when President George H. W. Bush and First Lady Barbara Bush are visiting Nantucket so he can bolster his political credibility. Fay also tries to sneak aboard so she can shake hands with Barbara Bush in order to keep her streak of touching every President's wife ever since Eleanor Roosevelt gave Fay a pat on the head when she was a little girl. Gail breaks up with J
With the airport fogged in, Brian entertains the gang with his hypnosis act and gets Roy to confess his deepest, darkest secret: he stole $250,000 from an old man at a local Norwegian restaurant and buried it in his backyard. As everyone excitedly digs up Roy's backyard, Brian wonders how effective his hypnosis was.
Roy reveals his wife Sylvia is not dead after all, but living in Boston after having deserted him abruptly sixteen years ago. Accompanied by Brian, Roy flies to Boston to win his wife back, only to find her life has taken a surprising turn without him.
Roy and Brian trick Joe into coming with them to a timeshare lecture in South Carolina, to which both Brian and Roy assure Joe that they know how to finesse these hucksters and can use it for free golf, but a rainstorm ruins their plan. Subplot: Antonio plays the only song he knows on guitar ("Michael, Row the Boat Ashore") over and over, entertaining the passengers, but annoying Helen.
Antonio turns to a sham marriage to stay in the country after finding out he's about to be deported. He struggles to follow through—and fool the feds—when the only wife Brian comes up with for him is a crazy, homeless old bat that wants too much money.
Helen learns that she will get arrested for matrimony fraud if she divorces Antonio before three years have elapsed, unless he wins a green card in a lottery. Antonio is ambiguous about whether or not he won, suggesting he has genuine feelings for Helen. (Part 2 of a two-part episode.)
Fay is upset when Joe declines to give her a raise, citing budget cutbacks. But when Joe appears with expensive sheep-lined bomber jackets for him and Brian, Fay is outraged and quits. Joe has to eat several slices of humble pie to convince Fay of their partnership. Note: This episode shows a flashback of how Joe met Fay when she was a stewardess, and they decided to start Sandpiper Air.
Joe and Brian's childhood home is due to be demolished after a severe storm condemns it. At first they're upset, but then they can't really recall many happy memories of being there.
Dr. Frasier Crane's plans to conduct a self-esteem seminar on Nantucket are interrupted by Helen's accusations that he ruined her life in New York City when she attended one of his seminars. Instead of the refund she desires, Frasier allows Helen to attend the seminar for free to see if her problems can be solved.
Joe announces Sandpiper will give a plane ticket anywhere to whoever makes the biggest donation to charity by a specific deadline. Cranky Carlton Blanchard (William Hickey) wins by donating $10,000. The catch is Carlton wants to fly cross-country to reunite with his estranged brother, and along the way, annoys everyone on the plane. Furthermore, Carlton has a dull memory, as he cannot recall whether his brother lives in Rock Springs, Wyoming or Las Cruces, New Mexico.
Helen wants a new goal in life and takes an aptitude test. When the results are in, the gang intercepts the letter and sees her best skills are food service and musician. In order to avoid the forthcoming guilt, anger and depression from her, Brian falsifies the paper, which prompts Helen to aspire to become a stand-up comedienne. Guest appearance by Oliver North as himself.
Joe, Brian, Helen and Lowell try out a video dating service and compare notes to each other's experiences. Brian gets matched up with a pushy trader (Peri Gilpin), Helen gets matched up with a local waiter who conscripts Helen into his work, Joe gets matched up with a ventriloquist who will not talk but her dummy has a crush on Joe, and Lowell gets matched up with an ordinary woman, but his idea of a fun date is to take her on a ride on the forklift.
Brian gets a large tax refund and treats himself to an expensive vacation in Barbuda. When he learns the refund was in error and the IRS is demanding the money back, he is subject to a tirade from responsible Joe, who advised him to save the refund instead. Brian gets a second job as a security guard at a bank to earn the money. In the subplot, "Responsible Joe" seems to only be so in financial matters, as he is taking a girl he is dating to Fenway Park for an opening day Red Sox game despite th
Joe is reunited with his old baseball coach Snyder (Brian Doyle-Murray) who touts his new star pitcher Ty Warner (Matthew Fox) who is poised to break Joe's longstanding record at Siasconset High School for the most strikeouts. This causes Joe to feel both anger and jealousy at his age and station in life.
In a bizarre twist of fate, Helen spilling soup on a man lands her a job offer with the director of the Boston Symphony Orchestra. She fights to get even one person (besides Roy) to attend her inaugural performance, but in the end, they'll all wish they'd stayed on the island.