When Helen and Casey's mother arrives on Nantucket, Helen isn't sure which sister her mother came to see. And when she finds out her mother gambled away the $10,000 for her and Joe's wedding, she is convinced that Casey has always been the favorite of the family.

Meanwhile, Fay and Roy split a ticket to a Barbara Streisand concert; Antonio adopts Deedee as his own mother; and Lowell and Brian stuff themselves on Deedee's food in an attempt to see who can out-eat the other.

With nothing to do one Saturday night, Joe and Helen start socializing with a new couple on the island, the Tuckers. Their initial trepidation is soon forgotten in all the fun, but the Tuckers quickly tire of their needy counterparts.

Meanwhile, Brian and Casey start hitting the singles hangouts together and Antonio becomes Lowell's "hands" when Lowell injures his working on the cab.

When Roy flies in a mail-order bride from Russia, Helen tries to convince Roy and Anya that this marriage should never be, but both ignore her. Anya's resolve is weakened by a chance encounter with another man, and the sight of her weeping just moments before their wedding convinces Roy to free her from his commitments to him.

Meanwhile, Fay convinces Lowell to pretend to be her lover to impress her soon-to-arrive friends, but Lowell insists on cramming and it finally gets to Fay who calls the whole thing off just moments before they are to arrive.

Struggling to agree on wedding plans, Joe and Helen decide to crash another couple's wedding to check out a place. Unfortunately their fighting infects the newlyweds. At the airport later, seeing the newlyweds about to take seperate honeymoons, Joe and Helen try to right their wrongs and bring the newlyweds back together.

Meanwhile, Lowell and Antonio train for a Polar Bears competition.

The Gang make preparations for the upcoming Siasconset High School reunion, but the events of the reunion are not what anyone expects.

After receiving the news that he might be the father of Sara's little boy, Jason, Joe is advised by Roy to keep quiet on the whole affair, but Joe's guilt forces him to tell Joe and Helen.

Meanwhile, Lowell questions his choice in careers and Antonio struggles to make Casey his valentine.

Brian's excitement over appearing on a talk show is dampened when his ex-girlfriend Alex also appears. After bitter words on and off the screen, the two sleep together, but Brian decides to end things.

As the wedding draws near, Brian struggles to come up with a gift idea for Joe and Helen. He finally hits on the idea of making a video for them, and goes about capturing everyone's memories of their relationship on video.

Carlton's ill health becomes a boon to the gang when Carlton's nephew Lewis invites them over to Carlton's house to start selling off the old man's items. Joe and Helen have an eye for the house itself; Brian drools over a classic muscle car; and Roy looks for furniture. But all is for naught as Carlton's health makes a swift turnaround.

When Helen discovers that she and Antonio are still married (by finding papers under her cash register), she turns to Roy for help. He convinces her she needs to fly to Mexico over the weekend to get a quickie divorce, but that means sending Joe out of town on a weekend fly fishing trip. But Helen's plan are strained when Antonio brings in a priest for an annulment and Joe's flight is delayed.

Joe and Helen's wedding day gets off to a bad start when the best man and maid of honor, Brian and Casey, oversleep after spending the night together. When Antonio discovers this, he and Brian fight. In the struggle, the wedding ring is lost down the toilet, followed quickly by Joe's searching hand, which gets stuck.

Joe and Helen return from their honeymoon in Jamaica to receive bad news: a night of passion between Brian and Casey in Helen's house resulted in a devastating fire. That leaves Brian kicked out of both the house and Sandpiper by Joe.

When digging through the rubble of Helen's home, Brian and Casey unearth a suitcase and photograph that had been the Hackett brothers' only inheritance from their late father. Brian's attempts to remind Joe of that fail, but Joe later sees a vision of his late father and forgives Brian. Meanwhile, Antonio executes his revenge on Brian and Casey and Helen takes out her anger on Casey's clothes.

Back from vacation, Lowell goes out for a meal of hot wings with Antonio and lands in hot water when he witnesses a mob hit. After he is threatened by the gangster's lawyer, he decides to join the Witness Protection Program and leave Nantucket forever, rather than see the gangster released and have a chance to kill again.

Joe and Helen reap unpected benefits after getting a large insurance settlement for Helen's burnt down house. But Joe soon faces the task of stopping Helen's shopping spree before it leaves them broke.

Meanwhile, Brian and Casey try to find something in common and Antonio returns to Edna, "The Big Faced Girl."

After fighting with Helen over the architect's plans for their new house (he wants a big screen TV in the bedroom, she wants a walk-in closet), Joe has a strange dream involving Tigers, Clowns, Roy belly-dancing, and the couple dying in a plane crash with Antonio. As one by one the dreams events come to pass, Brian tries to convince Joe to heed the dream's warnings, but he fails. Joe, Helen and Antonio soon find themselves plunging to earth in the plane…

Nothing goes right at Helen's christmas party: Joe wants to hit the road to head for the slopes before they are snowed in; Antonio gives but does not receive; Roy misses his mother; Budd tries to be social; and Casey invites Carlton's annoying nephew Lewis.

Joe and Helen volunteer to babysit but it's far from the learning experience that they hoped it would be. Meanwhile, Casey gets a big time Hollywood star to come to the island to appear in her Nantucket Tourism commercial.

It's Roy's 12th birthday (he was born on a leap year), and Helen contacts Roy's son R.J. and convinces him to come back to Nantucket for the party. But the initial reconciliation is dashed when R.J. brings his significant other to the party.

Meanwhile, Brian helps Antonio out by driving the cab while Antonio waits for his driver's license.

Fay quickly falls for Lyle, the dashing man she met on a cruise, but the wedding is jeopardized when Fay learns the awful truth about him. His real first name is George, just like her first three dead husbands. Armed with this new knowledge, Fay decides against marrying a fourth George and calls off the wedding.

When news arrives that Davis Lynch has re-surfaced, Helen recounts the tale of how she never broke off her engagement with him, then tries to break the news to Davis, while not alerting Joe.

Sandy's return sends Joe to the psychologist, as no one believes his stories of her obsession with him. The psychologist does wonders to calm Joe down, but the real psycho is revealed when Joe meets Sandy in the vacant psychologist's office.

Meanwhile, Roy, Antonio, Fay, and Casey try to deal with the news they may have suffered food poisoning from Helen's tuna.

Antonio thinks his fortunes have taken a turn for the better when one of passengers hires him to be his personal chauffeur. But some overheard conversations seem to indicate that his new boss is a mobster.

Meanwhile, Helen hurriedly reads "Don Quixote" when her old English Literature teacher from high school drops by for a visit.

The contractor Joe and Helen hires to build their new house falls apart when his wife kicks him out, and the Hacketts try to rebuild his confidence and get him back to work.

Meanwhile, a vacationing George Kennedy is bothered by an annoying fan: Brian.

Antonio meets the perfect woman, but when she disappears before he can get her name, he goes on a desperate search for her, only to discover it wasn't just coincidence that she was so difficult to track down.

Meanwhile, Brian impresses Helen with his ability to read women and predict the entire relationship before it even starts.

The unearthing of a 20-year old time capsule is occasion for Joe, Brian, Helen, and Casey to reflect on what kind of a future they envisioned themselves having as kids. Joe dreamed of being a pitcher for the Red Sox, Brian dreamed of being a suave secret agent , and Casey dreamed of being a supermodel—but only Helen's dream came true.

Joe faces a moral dilemma: can he lie to Helen so he can go to a strip club with Brian? To soothe his conscience, he volunteers some time at the Golden Crest retirement home, but ends up taking one of the residents with him to the strip club.

Meanwhile, Fay and Antonio write their own eulogies.

Burdened with continual problems by living with Brian and Casey, as well as further delays in the building of their new house, Joe and Helen decide to buy another house. They solve one problem by selling their old new home, but another presents itself in the last moments in the old Hackett house.

After Joe and Helen burn down Brian's house, he's expecting a big check, much like the one Joe and Helen got. But the gutting of the old Hackett house is cause for an appearance by an insurance investigator, who has serious doubt about the legitimacy of the two claims in the last year—until she and Antonio's wild night of passion sparks a blaze at the local hotel and that convinces her the cases are legit.

Joe and Helen meet the next-door neighbors, Steve and Barbara, but what starts out as pleasant soon turns disturbing when Steve asks for $5000 to cover his gambling debts. Becoming increasingly paranoid after a fight, Joe and Helen decide to try and make amends, only to find out their new neighbors are only on the island for the month.

Meanwhile, Antonio receives his Uncle Bernardo's personal affects after he dies, including a set of perfume scented love letters appearantly from Bernardo to a certain very famous movie star of the times (Gina Lollobrigida). Hearing this, Antonio suddenly becomes a suave ladies' man with confidence, until he finds out his Uncle wasn't in love with Gina, but Gino.

Casey encourages Brian to use his insurance money to open a martini bar, offering to help manage it. But things go awry immediately when the first customer through the door slips and falls on the floor. Brian's problems are compounded when he learns Casey never got insurance.

Cord's first act as the new President of Sandpiper is to hold a meeting, informing everyone they need a "big idea". Something that drives Joe crazy, trying to get everyone to see there is no "Big Idea". But Roy mentions to Cord that the charter business is the one, he hasn't been able to crack.

Roy's "Big Idea" pays off when Sandpiper becomes the charter for singing sensations, the Todds.

When Cord chickens out on delivering a presentation before his father's board of directors, Joe and Brian must deliver it.

Meanwhile, hanging in the men's, Helen learns a nasty secret: Cord was expected to fail at Sandpiper for the tax write-off.

On their way home from Las Vegas, Joe has a bad case of food poisoning and is soon helpless in the airliner's bathroom, where he is soon followed by the plane's pilots. This leaves the job of hero to be played by Brian, who safely lands the plane and becomes an instant celebrity.

Joe tries to deal with Brian's newfound celebrity and all the grief he's getting from Helen over his "Men's travel bag", but Brian's celebrity is short lived and he soon is back at Sandpiper asking for his old job back once again.

After selling off the valuables of her George's, Fay is visited by their ghosts, demanding that she buy back their items.

Meanwhile, Joe's Valentine's Day efforts seem paltry to Helen compared to the man intending to propose to his beloved with a banner flying from the Sandpiper plane, and Brian and Casey prepare to go out on a sham date.

Brian and Helen's trip to New York to see "Rent" turns into a nightmare when the theatre refuses to transfer the tickets from Helen's benefactor to her. Even worse, a con-man robs them of their money and Helen is forced to compete in a drag queen contest in order to get the money to get home.

Meanwhile, a bad back leaves Joe in the house alone with a suddenly talkative Antonio.

Kicked out by Joe and Helen, Brian and Casey move into a new home with Antonio. Meanwhile, Joe and Helen's fling with nudism has them being threatened with blackmail when the neighbor kids snap pictures of them.

When a long time rival drops out of a boxing tournament, Joe finds himself matched up against Brian. But what starts out as a friendly competition gets decidedly unpleasant.