Everyone is of course skeptical when Brian announces that his relationship with Alex is special. To try to ensure that their relationship lasts longer than a couple of weeks, they decide not to sleep with one another yet.

Roy meddles in everyone's personal lives, causing problems for everyone.

The gang reluctantly convince Lowell to divorce Bunny. After the papers have been signed, Bunny comes on to Lowell and they start sleeping together. When the gang finds out Bunny has a fiancé in Boston, Faye decides she must tell Lowell.

Joe brings a guy to the island whom he hopes will invest in Sandpiper so that Joe can expand the business. But when the guy sees Helen, he asks Joe to fix them up. Joe asks Helen to go out with him and she reluctantly does. It's after that Joe realizes that he used Helen and tries to get her out of it but she's fallen for him.

Alex and Brian's plan for a romantic weekend does not go as planned.

While trying to create a perfect evening with her boyfriend, Davis, Helen runs into obstacle after obstacle with various friends who assist in aiding with what can only be certain disaster.

Episode begins with what appears to be Joe's lifeless body floating in water and we hear his voice telling how he got to this point. It began when a passenger is looking for his briefcase that he left on the plane and was not returned to him. And he demands that Joe locate it. And that's when everyone starts dumping on Joe: Antonio wanting Joe to co-sign for him when he goes to the bank to apply for a loan to buy a new cab, Brian is concerned that his first intimate moment with Alex was not outstanding, Helen concerned about her relationship with her boyfriend, and Fay (who learns that one of her late husbands is being transferred to the same cemetery at which another one of her husbands is buried) asks Joe to keep it from happening. And Roy keeps on playing a radio commercial for his service on tape and Lowell is tinkering with a motorcycle that drives Joe mad. And when a reporter from the newspaper of Joe's alma mater comes to interview him, and brings up the fact that Joe didn't do the things he set out to do. Joe's about to snap.

With Joe still gone, everyone is wondering where he is and when will he return, especially Brian who's worried about the business. When Joe's credit card bill arrives, Brian learns he was last in Mustique. So he goes there to try and find him and does. But Joe doesn't want to go back cause he's still having fun. Brian reminds him that the business needs him. Joe then turns control to him. Brian returns and finds himself swamped. And his relationship with Alex suffers. And things get worse when the bank takes the plane.

Joe's old schoolmate comes to town for a visit. Is everything as it appears?

Joe, Brian, Helen, and Lowell take off in search of an adventure.

Antonio has the Christmas blues and Faye is hosting the children's Christmas party.

Davis comes to the island and brings Helen out and invites Joe, Brian, and Alex to come along. They go back to his hotel room and while he goes to freshen up, Helen goes through his luggage and finds a present which she assumes is for her and sees it's something extremely personal. When he tells her that he has something for her, it's not what she saw. So she wonders if he's seeing someone else.

Joe and Brian are tired of Lowell, who has been staying with them since Brian sank his boat, bossing them around want him out of the house, so they try to get him to buy his own place. But when they find him staying at the airfield instead of his new place, they learn that Lowell has never been on his own before. But when Roy tells him a "story" about his "brother" whom he never saw after he "left", Lowell decides to give it a shot.

Fay is feeling spooked when friends tell her that someone has been asking questions about her. When a Private Investigator shows up at the airport, she's not sure what to expect. The man who hired the P.I. shows up and tells his story; He was a soldier who went to a USO dance where Fay volunteered, back during the Korean War, who then went off to war owing Fay a dance, and he's finally arrived to get that last dance. Meanwhile, Antonio gets an illegal cable hookup from a friend of Roy.

To help pay for his new used cab, Antonio gets a job as a chauffeur for Carlton Blanchard. Things get even worse when Carlton's equally annoying nephew, Lewis, arrives on Nantucket to attend Carlton's banquet.

Joe begins dating a 19 year old girl whom Helen used to babysit.

Brian's exclusive commitment to Alex is sorely tested when Joe flies in a group of models for a photo shoot. Meanwhile, Helen's decision to name food items on her menu after the people in the airport doesn't go as well as she would have hoped. Lowell takes forever deciding what he wants to be, but finally suggests "LowellSlaw" and Roy objects to being associated with the Giant Turkey Leg.

To ease Alex's embarrassment over having to take a job as waitress during the off-season, the gang tell their own stories of off-season jobs. Joe flew a star chimpanzee, Fay dressed up as a Giant Lobster, Antonio sold funeral plots and Brian and Helen performed a magic act for Roy's Lodge.

Brian and Alex suffer the annoying habits of each other after deciding to move in together.

Coach Mattay visits the island and resumes belittling Joe and Brian just like he did back when they were in high school. They decide to play a prank on him that gets way out of hand.

The appearance of Roy's ex-wife Sylvia on Nantucket surprises the gang as much as it delights Roy. Roy hopes for a reconciliation, but after a phone call comes into AeroMass saying that she was only doing it to get even with her cheating ex-husband, Brian reluctantly tells Roy. Roy refuses to believe him at first, but eventually skips out on sleeping with his ex. Meanwhile, Helen tries to fend off a smitten and slightly crazy waiter from the crab house.

Davis cancels yet another date, so Helen decides to go out with another man. When Joe's date with Sandra suddenly comes into conflict with his date with Joy, Joe decides to lie his way out of his date with Sandra. Joe's lies come back to bite him, as Joy cancels on him. Davis shows up on the island after all, only to find out Helen is out with another man. So he treats Joe to a night out at the Club Car, where Helen and her date show up, followed quickly by Sandra. Joe ends up busted while Davis and Helen go elsewhere to reconcile.

When Brian's old friend Danny arrives on the island, the two start reliving their old wild lifestyle, and Alex begins to feel neglected. Things come to a boil when Brian returns from an all night party in New York City. Alex tells him to pack up his stuff and get out of her apartment and Brian's final plea at the end fails. Meanwhile, Lowell is taken advantage of by his childhood idol, Big Strong Man.

Davis proposes to Helen and she accepts, re-igniting old feelings between her and Joe.