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.
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.
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 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.
Joe's efforts to raise more money for Sandpiper seem to be on the verge of paying off; he awaits word from the bank loan office. Meanwhile, Helen is distraught at the news of Davis' mid-week arrival. She is sure Davis is coming to break up with her. But Davis surprises her with a marriage proposal, and she readily accepts. She leaves to go home to pack for her flight to New York that night just as Joe arrives back from the bank, with the good news that the bank has agreed to the loan. Stunned by the news of the marriage, Joe goes over to Helen's house. Joe and Helen ...
Brian's going to a psychiatrist to deal with his break up with Alex and is grown dependent on him. Joe and Helen see him and he makes a remark that makes them think they're not suitable for each other. And Lowell is looking for his hat.
After his therapist pronounces him fully recovered from his break-up with Alex, Brian plunges back into the dating world. His efforts at the Club Car yield nothing of interest (despite Antonio's assistance with the "Good Cop, Bad Cop" routine), so he follows the advice of others and starts dating casual friend Joan. That elusive "spark" that is missing from their first three dates finally comes to life when Brian breaks up with her. Meanwhile, Lowell prepares a commencement speech address for his alma mater and Casey has trouble getting a good haircut.
After receiving 20,000 dollars from the family trust fund, Lowell invests the money in an old wax museum. Despite everyone's doubts about it, Lowell renovates the museum, but at the lackluster grand reopening of "Lowell Mather's House O' Wax", he comes to realize it won't be easy. When news comes of a disastrous fire at the museum, Lowell is determined to start again from scratch, but when he realizes that the place is fully insured against fire, he's thankful just to have his money back.
Joe and Helen just want some time alone with one and another, but Brian and Casey continually interrupt them. To apologize, Brian and Casey decide to surprise them with an engagement party, but Antonio misinterprets an overheard conversation and believes Brian to be sleeping with Casey. When she hears about it, Helen drags Joe to the party site well before they are expected.
Miss Jenkins, the gang's former teacher returns to the island to teach. And the boys had a great crush on her. Brian asks her out and he takes her home and she spends the night. Joe and Helen learn she spent the night. Joe praises Brian till her learns what happened between them. And Roy learns that a guy is dating his mom and wonders why?
Helen's mom comes to the island and she's hoping she'll give her money to help with the wedding as she did with Casey. When she arrives, Casey (who hasn't told her mom that her husband left her) pretends that he is out of town. When she gives Helen the check she's shocked at how little it is. At the same time Brian and Lowell compete to see who can eat more of her food. And Antonio clings to her.
Brian tells Joe they need to drum up more business, and suggests that they hire a celebrity spokesman and the man Brian wants him to consider is Ace Galvin, a former astronaut. Brian brings him over to the island and while trying to schmooze him, he goes around like a wild man which makes Joe wonder if he's the right man. But when it comes time for him to sign, they learn that Roy snatched him. Roy spends his time gloating until he learns of his latest antic.
It's Christmas and everyone has plans: Joe and Helen are going to spend it "together", Casey is going to Boston and sneak into a party, and Antonio is going to "get together" with the woman he's been seeing. Bob, the tower controller, comes to Helen for his usual coffee and jelly donut but Antonio took the last one and Bob freaks out. Antonio tries to offer him another donut but he instead puts a gun on Antonio and demands a jelly donut. While waiting, Bob tells Antonio that things are not good because for one thing his wife is seeing another guy. When Helen makes ...