After a ten month silence, Joe hears from Helen in New York City. Learning she has failed in her music endeavors, he convinces her to come back to Nantucket but doesn't mention that he has a new girlfriend.

Following Helen's damage to his office, Joe tries to get her to pay for the damages. When she refuses, Joe decides to sue her.

Helen's anger issues with Joe continue to escalate so others convince her to go to a group therapy session.

Lowell is paranoid that his wife Bunny is committing adultery.

When Roy's competition for the town council drops out, the gang convince Joe to run against him. However, the local newspaper endorses Joe's campaign manager, Fay.

The arrival of a wealth woman has Fay, Roy, and Helen eager to tap into her wealth. But she only has eyes for Brian and he soon enjoys the lavish gifts and lifestyle she heaps upon him.

As his birthday approaches, Joe firmly insists that the rest of the gang not throw him a party. The delivery of a large crate to the hangar convinces Joe that the gang wants to surprise him anyway.

Tired of the bickering between Helen and Gail, Joe suggests that the two go out to lunch together. Meanwhile, Fay has an opportunity to keep her streak of touching First Ladies alive as the president and his wife come to the island.

With the airport shut down due to fog, the gang tries to find ways to pass the time which leads to Brian doing his hypnosis act on volunteers.

Pressured by questions, Roy admits that his wife Sylvia is not dead but that she left him years ago and is living in Boston.

Brian talks Joe into a vacation so they can do a little golfing only to find out it's actually a free weekend at a timeshare resort in exchange for attending a high-pressure sales pitch. Meanwhile, Antonio learns to play the guitar but only knows one song which everyone quickly grows tired of.

Antonio receives a notice that he faces deportation when his green card expires so Brian attempts to find him a wife so that he can stay in the country.

Helen resigns herself to life as Antonio's wife but she soon sees an opportunity to help him get a new green card in a lottery.

Fay is understanding when Joe tells her he won't be able to give her a raise but when she sees the brothers gloating over a pair of new leather flight jackets, she is outraged and quits.

The news that the Hacketts' old house has been condemned due to storm damage has the two brothers reminiscing about their childhoods.

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.

Joe is pleased to learn that the ticket he donated to the children's hospital's charity event brought in a huge sum. However, an error on the ticket force Joe and Brian to fly a cranky old passenger on a cross-country trip to find his long-lost brother.

After her short-lived career in real estate ends in disgrace, the gang convince Helen to take a job placement exam. When the exam suggests she should pursue a career in music or food service, they decide to change it to something more exciting.

Antonio's stories of success with a video dating service have Joe, Brian, Helen, and Lowell trying their luck and betting on who went on the worst date.

After returning from a vacation made possible by a hefty tax refund, Brian finds out that the refund was an error. To help pay off his debt he takes on a second job as a security guard at a bank. Meanwhile, Antonio leaves for a trip to his home country of Italy and no one seems to care.

To help commemorate the anticipated breaking of Joe's old high school strike out record, his old coach coerces Joe to fly him and his star player to the game.

The gang accompanies Helen to Boston after she lands a gig with the Boston Symphony Orchestra. Caught up in a heavy storm and their fate uncertain, Helen recounts the bizarre way in which they got to that point.