10 months after moving to New York, Helen calls Joe to say hi. Joe doesn't tell her that he's been seeing someone else. Later he talks to everyone looking for someone to tell him that it's best not to tell Helen. But Brian tells him he has to. So they go to New York and they find her working in a strip club. Joe tries to tell her about his new girlfriend but she tells him that she's down on her luck. So he tells her to come back to Nantucket, without telling her. When they arrive she finds out unexpectedly.

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 result in her attending a group meeting after the persuasion of her friends.

Joe and Brian discover that Lowell is sleeping at the airfield. He tells them that he and his wife, Bunny are on the skids because he thinks that she's throwing herself at other men. They tell him to try and work things out. So he takes his wife out. The next day, he tells them things didn't work out because he assumed she was hitting on a guy. He then asks them if one of them can talk to her. Brian offers to do but Joe thinks he shouldn't. When he talks she comes on to him and Joe walks in before anything happens. Now they have to tell Lowell he has to get away from her.

When Roy's opponent for a seat on the town council drops out, the gang convince Joe to run against him. But the surprise endorsement of Joe's campaign manager Fay, by the local newspaper, gives Roy more competition than he can handle. So Roy concocts a plan, involving a story about how he has never won anything his entire life. Touched by Roy's story of his embarrassing failures in grade school, Fay throws the election.

A wealthy woman comes to the island and takes a liking to Brian and it isn't long before he becomes her boy toy. The gang is hoping that Brian can get her to invest with them or donate to some benefit they're involved with. But Joe tells Brian that he should be ashamed of himself but is having too much of a good time to listen. Joe then decides to tell her what he thinks of her but she cuts him off by saying she wants to invest with him, that's when he changes his tune.

It's Joe's birthday and he tells everyone that he prefer not to celebrate it. Brian decides to throw him a surprise party and everyone agrees to help. Later Joe overhears them planning the party and he's touched. But later they all realize they have prior commitments so they have to reschedule. Fay then tells Joe that he has to stay and take receipt of some items that are going to be delivered to the hanger later and that everyone else has plans. Joe thinking that it's a ruse to make sure he's around for the party goes along with it. But when a man delivering a crate arrives, he thinks that they're in the crate and is expecting them to be inside but is disappointed that they're not. And the next day is sore at everyone for pulling a fast one on him. So Brian tells him the party was rescheduled and asks him to be there. And when Joe tells Brian of the assumption he made about the crate, Brian decides to do that. But the person Brian puts in charge of bringing the crate to Joe makes a mistake.

When Helen and Gail continue to bicker, Joe wants them to make peace. So he tells them to spend some time together and it isn't before long that they're buddies and talking about Joe's deepest secrets. When word comes out that the President will have a layover; Roy wants to get his picture taken with him and Fay wants to touch the First Lady which she has been doing with the last 8 First Ladies.

Under hypnosis, Roy confesses to a crime he did, now it's up to the rest to figure out what to do.

Pressured by questions, Roy reveals his wife Sylvia is not dead after all, instead living in Boston after having deserted him abruptly sixteen years ago. In the company of Brian, Roy flies to Boston to win his wife back. Roy's efforts are for naught, however, as Sylvia refuses to leave her life as the wife of a rich plastic surgeon to return to Nantucket with him.

Brian tries to scam a time-share out of a weekend of golf by signing up for a sales pitch he has no intention of attending. Joe, Roy, and Lowell tag along. The trip is ruined by a tropical storm in Florida.

Antonio learns that he's facing the possibility of being deported. They think the best way is for him to marry an American. So they try to find someone willing to marry him. But on the day that he told immigration that he's suppose to get married, the woman they found doesn't show up.

Helen marries Antonio to keep him from being deported. But she's dreading having to stay married to him for the time required for him to get his citizenship. But Brian learns of another way for Antonio to get his green card. And that is for him to enter the Green Card lottery, so Helen tries to get as many applications out so that he can get his green card and she can no longer be married to him.

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 quits. She accepts a position at Aeromass, while Joe struggles at Sandpiper. After Brian tells the story of how they met years ago, their differences are finally resolved.

Brian and Joe learn that the house where they lived is going to be demolished. While Faye tries to see if she can do anything to keep it from happening, they go to see it one last time. And they remember when they first moved in and how things were when their parents were still together. And they even recall how they first met Helen.

Frasier Crane comes to the island to conduct a workshop. And it's while conducting his workshop that Helen sees him and says he's the man who ruined her life. it seems that he advised her to leave the island and go to New York. Frasier brings her on stage to talk and while he fails to convince her, it was not his fault, he passes the buck to Joe. Who then stands up and says he did nothing.

Joe donates a free trip to a charity auction. And the man who bought is Carlton Blanchard, an old man is not quite all there. When asked where he wants to go, he answers Las Cruces, New Mexico which is not where they usually go. At first, they're not willing to do it but when he tells them, he's going to see his brother whom he hasn't seen in years, they give it a shot. Lowell and Antonio tag along.

When Helen loses her job as a Realtor, she finds herself wondering what's she's going to do now. Antonio suggests she take a test that determines what job she would be suitable for. She takes it but when the results arrive, Antonio saw the results and tells everyone that it said her choices were either music or food service. The gang thinks they should change the results. So Joe tells Fay to put in law which is something Joe says she was interested in before. When Fay asks what should she put on the second choice, Joe tells her to put something. Helen reads and is more taken by the second choice, stand up comedian, so she tries to get her routine ready.

The gang goes on dates through a service and meet up at the Club Car to tell their odd stories.

After returning from a vacation made possible by a hefty tax refund, Brian finds out that the refund was an error. To help pay of his bet he takes on a second as a security guard at the bank. But he's fired after a robbery and it's back to flying. But while flying Antonio to Boston he discovers the robber is on board the plane. Unfortunately, the robber also recognizes Brian and pulls a gun out to force Brian to land in a field. Brian dares the would be Hi-Jacker to kill him as the plane is screaming towards the ground, the robber gives in first and hands the gun to Antonio. Meanwhile, Antonio leaves for a trip to his home country of Italy and no one cares.

Joe's old baseball coach wants him to bring the player who's poised to break Joe's record. While on route, Joe learns that the player among other things will be getting a car and Joe will be the butt of some jokes. When the airport tells Joe that it's not uncertain if conditions are good for him to land but they want him to make that decision and he decides not to making people think he didn't want the player to break his record.

The episode begins with everyone in a plane headed for Boston but they're caught in a storm and uncertain of their fate. Then we see how they got there; it began when Helen got an opportunity to perform in Boston. But everyone can't make it because prior engagements. Then somehow everyone becomes free.