After a ten month silence, Joe hears from Helen in New York City. When Helen fishes around about there relationship, he can't bring himself to tell her about his new girlfriend, Gail. Joe and Brian travel to New York to tell Helen in person, but her NYC experience hasn't been all she claimed.

Helen refuses to pay for the repairs to Joe's office, even after she ran her Jeep through it. As matters escalate, Joe winds up struggling to find someone to deliver a subpoena to Helen after suing in small claims court.

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 is paranoid about his wife, Bunny, flirting with other men. When Brian offers to help by talking to Bunny, he gets more than he bargained for.

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.

Tired of the bickering between Helen and Gail, Joe suggests that the two go out to lunch together. Things go farther than he expects, and the two women become fast friends, comparing embarrassing notes about him. Meanwhile, when the president and his wife visit Nantucket, Fay tries to maintain her streak of touching every first lady since Eleanor Roosevelt.

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.

Brian talks Joe into a vacation so they can do a little golfing, but neglects to tell him it's a time share weekend promotion. Roy and Lowell tag along and disasters mount. Meanwhile, Antonio discovers money to be had in playing guitar for tips at the airport but only knows one song.

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.

Stunned by the news that their "quickie" divorce won't be for another three years, Helen sadly resigns herself to life as Antonio's wife. But she gains new hope when Brian tells her about a green card lottery.

Fay is forgiving at the loss of her annual raise when Joe tells her how tight money is, but when she sees the brothers gloating over a pair of new leather flight jackets, she quits. She takes a position with Aeromass while Joe struggles at Sandpiper.

Joe and Brian learn their childhood home has been condemned due to storm damage and all efforts to save it fail. The gang visits one last time before the wrecking ball flies, and they relive some childhood memories.

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 is thrilled to learn that, for a charity auction, a plane ticket he donated to fly to any nearby airport goes for a staggering $10,000. But his mood sours when a misprint on the ticket forces him to fly crabby old Carlton Blanchard on a cross-country trip for a reunion with his brother.

Stuck behind a lunch counter and facing years of rejection as a musician, Helen takes a job placement exam. When the exam suggests she should pursue a career in music of food service, her friends decide to change the results—to law career or stand-up comedian. To their shock, she runs with comedian.

Antonio's repeated success with a video dating service soon has Joe, Brian, Helen and Lowell plunging into the video dating fray, with less than stellar results.

Brian is forced to take a job as a bank security guard to cover a spent tax refund that he received in error. But on his first day, he fails to stop an armed robber and has to deal with the aftermath.

To help commemorate the anticipated breaking of Joe's old high school strike-out record, Joe's old coach coerces him to fly him and his star player to the game. But when heavy fog prevents his landing on time, some question whether his concern was safety or for his own high school record.

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.