In the series premiere, brothers Joe and Brian Hackett search for a suitcase full of cash that their dead father supposedly left them.

Fay encourages a retired pilot to complete his trip around the world.

Brian flys to Boston to see if he can reunite with his ex-wife Carol.

Joe and Brian compete to see who Carol loves more.

Brian sets Joe up on a date with a woman who's been with every man on the island.

Joe spies on Brian and Helen when they go on a date.

Brian hires an actor to play the role of a charming pilot who asks Helen out.

A magazine writer wants to do a cover story on Joe, but then he meets Brian, and finds his life more interesting. Cliff Clavin and Norm Peterson visit the island.

Helen plays her cello to a very famous conductor (special guest star David Ogden Stiers), who tells her she's terrible.

Roy tries to make friends with the gang by joining them in a game of Trivial Pursuit.

Joe holds a bachelor party for a guy he can't remember going to high school with.

Joe and Brian compete to see who gets Helen a more expensive birthday gift.

Brian dates a policewoman to get her to drop charges on his unpaid parking tickets. Meanwhile, Lowell totes his video camera around the airport trying to capture something to submit to the show "America's Wackiest Videos."

Joe's grounded due to high blood pressure and he wonders if Helen will go out with him, now that he's not a pilot.

Joe and Helen go on their first date and Brian hires high school student Kenny McElvey as a backup pilot for the grounded Joe.

Roy gets the surprise of his life when he agrees to let his star athlete son take cello lessons from Helen.

After everybody's holiday plans fall through, they decide to surprise Faye at her Christmas party. When they arrive, they discover she'd lied about her plans and find her all alone.

Helen decides to take flying lessons from Joe but his classes are too long and boring so Brian offers to let her fly the plane. Shortly after, Brian is injured and Helen finds herself behind the controls.

Joe plays nursemaid to Helen when she has her wisdom teeth pulled, but loses his patience when he tries to sneak away to watch a basketball game.

Brian tries to save face when Fay trounces him in a friendly game of tennis.

When Joe's back goes out and forces him into a stay at the hospital, Brian takes over Sandpiper. His eagerness is soon deflated when all his new ideas and crazy promotions turns into a disastrous mess.

During a cargo flight, Brian and Joe see a UFO. Joe's concerned about unfavorable media attention, but Brian wants to report the sighting to the FAA. Meanwhile, Helen and Fay end up arm wrestling over a lunch bill dispute.

When Joe and Helen decide to meet at their "special place" on Valentine's Day, they end up on opposite ends of the island. Meanwhile, when Roy's blind date exceeds all his low expectations, all he can do is try and figure out what's wrong with her.

Joe and Helen find themselves being rushed to the altar when Brian and the jet-setting woman of his dreams talk them into a double wedding.

When Brian starts to date Kenny's mother, Kenny is worried about Brian's reputation with women. But just as Kenny warms to the idea of them dating, Brian dumps her. Meanwhile, Joe and Helen squabble over the issue of privacy.

Brian is ecstatic when he and Joe's mother returns to Nantucket years after deserting them and their father. For Joe, it's too little too late, because he can't forgive her for leaving.

While the house is being fumigated, Brian is forced to stay with Fay. The experience turns out to be surprisingly pleasant—that is, until he becomes convinced he's seen her featured on the "Most Wanted" show he is watching about a serial killer.

Much to Joe's surprise, Helen wins a job with the Maine State Symphony. But when Helen comes to Joe and tells him she would stay if he only asked, the discussion turns into a huge fight involving a fire extinguisher and a grease gun. Meanwhile, a confused looking woman who doesn't speak english and has been hanging around the airport gains Fay's sympathy and Roy's hostility.

After a ten month silence, Joe hears from Helen in New York City. When Helen fishes around about there relationship, he can't bring himself to tell her about his new girlfriend, Gail. Joe and Brian travel to New York to tell Helen in person, but her NYC experience hasn't been all she claimed.

Helen refuses to pay for the repairs to Joe's office, even after she ran her Jeep through it. As matters escalate, Joe winds up struggling to find someone to deliver a subpoena to Helen after suing in small claims court.

Concerned by Helen's persistent anger over her break up with Joe, the rest of the group convince her to seek help with a transition group, not realizing exactly who the group is for. Meanwhile, after escorting Helen to the group meeting, Brian becomes obsessed with talking about Carol and takes over the group.

Lowell is paranoid about his wife, Bunny, flirting with other men. When Brian offers to help by talking to Bunny, he gets more than he bargained for.

Roy's competition for the town council drops out, and the gang convinces Joe to run against him with Fay as a campaign manager. But when the local newspaper endorses Fay herself, Roy gets more competition than he can handle.

The arrival of Millionaire Mimsy Borogroves has Fay, Roy and Helen eager to tap into her wealth. But Mimsy has eyes for Brian, and he soon enjoys the good life, receiving expensive presents and accompanying Mimsy everywhere, much to Joe's disgust.

As his birthday approaches, Joe firmly insists that the rest of the gang not throw him a party. When Fay asks him to stay late to wait for a shipment of airplane seats, Joe becomes convinced they're throwing him a party anyway.

Tired of the bickering between Helen and Gail, Joe suggests that the two go out to lunch together. Things go farther than he expects, and the two women become fast friends, comparing embarrassing notes about him. Meanwhile, when the president and his wife visit Nantucket, Fay tries to maintain her streak of touching every first lady since Eleanor Roosevelt.

Out of boredom while the airport is shut down for fog, Brian tries his hypnosis act on volunteers, during which Roy makes a shocking revelation.

Roy reveals his wife Sylvia is not dead after all, but living in Boston after having deserted him abruptly sixteen years ago. Accompanied by Brian, Roy flies to Boston to win his wife back, only to find her life has taken a surprising turn without him.

Brian talks Joe into a vacation so they can do a little golfing, but neglects to tell him it's a time share weekend promotion. Roy and Lowell tag along and disasters mount. Meanwhile, Antonio discovers money to be had in playing guitar for tips at the airport but only knows one song.

Antonio turns to a sham marriage to stay in the country after finding out he's about to be deported. He struggles to follow through—and fool the feds—when the only wife Brian comes up with for him is a crazy, homeless old bat that wants too much money.

Stunned by the news that their "quickie" divorce won't be for another three years, Helen sadly resigns herself to life as Antonio's wife. But she gains new hope when Brian tells her about a green card lottery.

Fay is forgiving at the loss of her annual raise when Joe tells her how tight money is, but when she sees the brothers gloating over a pair of new leather flight jackets, she quits. She takes a position with Aeromass while Joe struggles at Sandpiper.

Joe and Brian learn their childhood home has been condemned due to storm damage and all efforts to save it fail. The gang visits one last time before the wrecking ball flies, and they relive some childhood memories.

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. Instead of the refund she desires, Frasier allows Helen to attend the seminar for free to see if her problems can be solved.

Joe is thrilled to learn that, for a charity auction, a plane ticket he donated to fly to any nearby airport goes for a staggering $10,000. But his mood sours when a misprint on the ticket forces him to fly crabby old Carlton Blanchard on a cross-country trip for a reunion with his brother.

Stuck behind a lunch counter and facing years of rejection as a musician, Helen takes a job placement exam. When the exam suggests she should pursue a career in music of food service, her friends decide to change the results—to law career or stand-up comedian. To their shock, she runs with comedian.

Antonio's repeated success with a video dating service soon has Joe, Brian, Helen and Lowell plunging into the video dating fray, with less than stellar results.

Brian is forced to take a job as a bank security guard to cover a spent tax refund that he received in error. But on his first day, he fails to stop an armed robber and has to deal with the aftermath.

To help commemorate the anticipated breaking of Joe's old high school strike-out record, Joe's old coach coerces him to fly him and his star player to the game. But when heavy fog prevents his landing on time, some question whether his concern was safety or for his own high school record.

In a bizarre twist of fate, Helen spilling soup on a man lands her a job offer with the director of the Boston Symphony Orchestra. She fights to get even one person (besides Roy) to attend her inaugural performance, but in the end, they'll all wish they'd stayed on the island.

After their plane plunges into the Atlantic en route to Boston, the whole gang finds themselves at each others throats and struggling for survival in a leaky lifeboat.

Joe's future is up in the air when Sandpiper Air is grounded by his insurance company, but Brian's plan to save the airline doesn't fly right with Helen.

Sandpiper is finally back in business but Joe's nose is broken by a man who mistakes him for Brian. At the surgeon's office, the doctor's observation of a bump on Brian's nose has him obsessing about getting a nose job.

Roy is struck out at Fenway Park by his own rendition of the National Anthem, and Fay commits a costly personal foul at work.

Lowell convinces Helen to go on a date with him.

Antonio upstages Lowell in front of the Tuesday Night Rat Club, while Brian and Joe are grounded by an attractive helicopter pilot.

Brian and Joe gain a new roommate after Brian accidentally sinks Lowell's houseboat.

Brian's ex-flame arrives from New York to rekindle the fire and it's up to his friends to keep him from getting burned again.

After having a few drinks, Alex asks Joe to drive her home and when he arrives late the next day everyone assumes that they spent the night together.

Joe is irritated about getting charged a rewind fee for a returned video tape which he believes was rewound.

Helen dates a guy with an annoying laugh. Antonio has trouble with his jerk neighbor.

Antonio performs his civic duty when he helps bring to court a suspected robber and then testifies against him. But then the suspect gets released on a technicality, and Antonio starts to fear for his life.

When Lowell demands a raise from Joe and Roy, shrewd bargaining tactics by Antonio and Roy leave Lowell dejected and jobless.

When Alex tells Antonio and Helen that she posed nude for Playboy while in college, the secret is just too good to keep quiet.

With an opening in a quartet, Helen wants to try out but her cello is on the bottom of the ocean. She gets a second job to purchase a new cello but things don't go as planned. Lowell, Faye, Roy and Antonio audition for a play.

Helen gets the quartet role but hates it. However, she doesn't know how to quit without letting Joe and Brian down. Faye, Roy, Antonio and Lowell practice for their awful play.

Hoping to impress Alex, Brian claims to know Clint Black. Helen and Alex are entertained while they expect Brian's scheme to attend a concert and meet him will backfire.

Joe and Brian, in heated competition, pull out all the stops in a transparent attempt to get closer to Alex.

Helen throws a surprise birthday for Nantucket's most unpopular resident, 70-year-old Carlton Blanchard, who threatens to become a permanent household fixture after suffering a fall in her home.

Weeb Gilroy's death has Lowell searching for the right words to eulogize his long time friend. Words fail him at the end and all he can think of is to finish working on the plane they built together.

The crew is invited to the wedding of the air traffic controller.

Alex finally agrees to a date with Brian, only to find out later it was all a set-up.

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

Roy gets bored and decides to have some fun at everyone else's expense.

Lowell and Bunny make their separation final by signing the divorce papers only to start sleeping together again. Meanwhile, Antonio consoles a woman who's cheating husband left his cellphone in Antonio's cab.

When Joe flies in a potential investor, he's more interested in Helen than Joe's airline.

Joe is upset at playing chauffeur to the other couples for their romantic trips off the island but it's everybody else who ends up suffering. Meanwhile, Antonio and Fay help Roy change his image to try to impress a new woman.

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.

Joe feels the weight of the world coming down on him as everyone comes to him to help solve their problems. As the stress mounts, he knows he must make a drastic change.

With Joe MIA, the burden of running Sandpiper Air falls all on Brian. As he struggles to keep things in the air, he gets a clue to where Joe ran off to.

When news arrives that Sandy Cooper is returning to Nantucket, Joe fears her high school obsession with him will return but the others think he's imagining things. Meanwhile, Antonio tries to raise money to send to his family and Roy is worried about a visit from his cranky mother.

Joe, Brian, Helen, and Lowell head to Boston for a night on the town but end up at a party that's more than what it seems. Roy, Fay and Antonio pool their resources to win a radio contest.

Lowell's ex-wife arrives on Nantucket for a friend's wedding. Brian faces the prospect of meeting Alex's parents. Joe deals with the loss of a tree and Fay becomes overbearing as Helen organizes a holiday party for children.

Davis finally shows up to see Helen after a string of cancellations. A furtive search through his luggage reveals a gift that may be inappropriate at this stage of their relationship. Fay rescues a lab rat from her experiments by her psychology professor, risking a bad grade and charges of theft.

Tired of Lowell's strictness, the brother's boot him out of the house. Despite his reluctance, Lowell buys a new house and tries to adjust to the experience of living alone for the first time.

Somebody is asking questions around the island in search of Fay and she's spooked. Antonio loves the new cable TV service that Roy's shady friend installed.

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.

To Helen's disgust and Brian's envy, Joe starts dating a 19-year-old co-ed. Roy and Antonio find a dog whose cute charm no woman can resist.

Brian's exclusive commitment to Alex is sorely tested when Joe flies in a group of models for a photo shoot. Helen's decision to name food items on her menu after the people in the airport doesn't go as well as she hoped.

To ease Alex's embarrassment over having to take a job as a waitress at a medieval themed restaurant during the off-season, the gang tell their own stories of embarrassing off-season jobs.

Brian moves in with Alex, and both quickly become irritated by the other's annoying habits. Meanwhile, Lowell attempts to come up with a name for his sister's baby.

When the football coach who belittled Joe and Brian in high school returns to Nantucket to be honored in a gym dedication, they plan a practical joke that gets way out of hand.

Roy's ex-wife makes a surprise appearance on the island. She seems to be up for a reconciliation, much to Roy's delight, but may have ulterior motives. Helen tries to fend off a smitten and slightly crazy waiter from the crab house she went to the other night.

Davis cancels yet another date leading Helen to accept a date with another man. As for Joe, after two dates conflict, he tells a lie to get out of one of them only to have the other one cancel.

When Brian's old friend shows up and they resume their wild, partying lifestyle every night, Alex grows increasingly neglected. Lowell takes in his idol, over-the-hill television superhero Big Strong Man, who takes advantage of his hospitality.

Joe may have finally found a bank willing to float him a loan to expand Sandpiper Air. Helen anxiously awaits Davis' mid-week arrival, sure that he's coming to break up with her.

After their night together, Helen tells Joe that it was all a big mistake and she goes to New York to marry Davis. While bemoaning his loss with Brian (who has sorrows of his own, when news comes that Alex has left the island for good), Joe comes to realize he has to win Helen back. He follows her to New York and finally catches up to her in the elevator on the way to Davis' penthouse.

The arrival of Helen's elder sister Casey to Nantucket sidetracks Joe's plan to give Helen an engagement ring. What was originally planned to be an evening for two at Lexington's becomes a party of four, with Casey along to catch up with Helen and Brian along to occupy Casey. Then, before Joe can give Helen his ring, Casey gives Helen an even bigger ring as a gift, and Joe's angry frustration brings the night to a halt. He apologizes later that night and gives her the ring, but once again Casey drops in to spoil things. Helen finally stands up to Casey, who then reveals that her husband has left her, and she has no where to go. So Helen invites her to stay with her for as long as she wants.

After Brian's depression over Alex's departure results in a near break-down during a flight, Joe suggests he go see a psychiatrist. Once there Brian makes a partial recovery, but Joe is the one with the true breakthrough, as he realizes that his earlier acceptance of Helen's suggestion of an earlier wedding date may result in trouble for him in the marriage. When confronted, Helen agrees on the original wedding date, until Casey sparks some doubts. Misunderstandings ensue, resulting in the wedding being called off. Meanwhile, Lowell attempts to find a hat that Antonio lost.

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, but the "spark" that was there during their dates is now gone. Meanwhile, Lowell prepares a commencement address for his alma mater and Casey has trouble getting a good haircut.

After receiving $25,000 from the family trust fund, Lowell invests the money in an old wax museum. Despite everyone's doubts, Lowell renovates the museum. but he comes to realize it won't be easy at the lackluster grand reopening of "Lowell Mather's House O' Wax". When news comes of a disastrous fire at the museum, Lowell is determined to start again from scratch.

Joe and Helen just want some time alone with one another, but Brian and Casey continually interrupt them. Brian and Casey decide to surprise them with an engagement party as an apology, 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.

To pay off a $1500 IRS fine, Antonio becomes the driver/errand boy/personal assistant to Gavin Rutledge, a businessman visiting Nantucket for a week for a real estate deal. Uncomfortable at seeing Gavin dating Casey, Antonio faces a major dilemma when he finds out Gavin is married. At the cost of his job, Antonio tells Casey about Gavin, and Casey shows her gratitude by giving Antonio a jewelry gift she received from Gavin. Meanwhile, Joe is Irked that Brian had an erotic dream about Helen.

The return of 9th grade English teacher Laura Jenkins to Nantucket reawakens the Hacketts' schoolboy crushes. For Brian, fantasy becomes reality when he spends the night with her, but to his embarrassment he doesn't perform. Meanwhile, Roy deals with a con man interested in marrying his mother for her social security check.

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.

To counteract Roy's Aeromass promotions, the Hacketts woo famous astronaut Ace Galvin as a celebrity spokeman for Sandpiper. Joe and Brian soon discover that Ace is as charming and persuasive in public as he is irratating and annoying in private life. Any hopes of signing him up are dashed when Roy beats them to the punch, but Roy quickly discovers just how obnoxious Galvin can be.

On Christmas Eve, new air traffic controller Bob snaps when Antonio buys Helen's last jelly donut, pulling out a gun and taking Antonio hostage. Matters for Antonio only get worse when it is revealed that his new girlfriend is also Bob's wife. Joe is eventually able to talk Bob into surrending his gun, but the others are not very appreciative of the means by which he does it.

When Sandy Cooper returns to the island, Joe fears yet another bizarre encounter with the obsessed woman. She tells him it was all a practical joke, and he believes her until a stop at Helen's house becomes Sandy and Joe's wedding day. Meanwhile, Fay forces the old '70s wardrobe of one of her dead husbands onto Antonio, and Lowell tries life as a vegetarian.

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.

When Fay decides to retire, Joe and Brian hire Casey to replace Fay at the counter. To the Hacketts' surprise, Casey works wonders for their business. When Fay asks for her old job back, the brothers face a predicament. Rather than fire Casey, they decide to keep both at the counter, and sparks soon fly between the women.

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.

Lowell's innocent birthday gift to Casey lands him a show at an art museum when Casey shows off the gift to a museum director. Determined to launch both their careers in the art world, Casey relentlessly pushes Lowell's artistic abilities to the limit to try and meet the show's deadline, but eventually gives up after discovering how stressed Lowell becomes. Meanwhile, Brian's efforts to finish a roll of film for Joe and Helen are not appreciated, as the prank ends up in the hands of Helen's parents.

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.

When Antonio's cousin Dominic and his fiancée Teresa visit Nantucket, Antonio finds himself struggling to ignore his feelings for Teresa. He succumbs to temptation during supper at his apartment, after Teresa voices concerns over problems with her relationship, but he ultimately helps Dominic win her back. Meanwhile, Helen's side of the family outshines Joe's when the wedding gifts start to arrive.

The night before the wedding, Helen warns Joe not to have too wild of a bachelor party. But it's Helen who ignores her own advice in a wild bachelorette party, while Joe suffers through the worst bachelor party Brian's ever thrown. Later that night, after the guys return, Casey accidently slips into bed with Brian, and neither feels like leaving the other's company.

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.

The sad news of Harrison Kingsbury's death in Miami is occasion for celebration at Sandpiper, as Kingsbury's oldest daughter hires the Hacketts to bring the body back to Nantucket for the memorial. But the brothers fly the wrong body back to the island, and it's up to Joe to impersonate the late Kingsbury at the funeral.

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.

To lift Antonio's spirits after he's dumped by the "Big Faced Girl," Joe and Brian set him up with a girl at the Club Car only to discover later that she's a very expensive hooker.

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."

Joe and Helen's initial fortune at landing famous architect Y.M. Burg to design their new house soon turn sour as he suggests a house shaped like a giant "7." Meanwhile, Brian hires a new mechanic, Budd Bronski, who attempts to live down a previous "incident."

When Joe is too busy with his new wife to spend time with him, Brian turns to food. He ends up trying to deal with his problems at a meeting of the "Eat-A-Holics." Meanwhile, Antonio tries to get used to tight shoes, after he pays $200 for them, and Casey gets hired by the Nantucket Tourism Board.

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.

Joe and Brian are thrilled at the return of Grandpa Hackett, but Helen isn't so sure he is who he claims to be. Meanwhile, Antonio refuses to continue a chain letter, which everyone else gets and passes along, and begins to suffer for it.

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.

A publicity disaster occurs when Antonio covers for the Hacketts so they can go to a hockey game. Antonio bumps the Bruins' abrasive star goalie Danny "Dead End" Connelly off a Sandpiper flight to a critical game, causing the Bruins to lose. Meanwhile, winter tourism on the island takes an upswing when Casey welcomes the International Society of Masochists to Nantucket.

Brian falls in love with a woman while flying her to Nantucket for her wedding. Meanwhile, Antonio has mixed feelings after finding out Roy is dating Edna, "The Big Faced Girl."

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.

On the verge of losing her job with the Tourism Board, Casey sees a solution when her sister city idea is accepted. But things go downhill when Brian sleeps with the visiting princess of prospective sister city Khirinan. Meanwhile, Antonio offers to take the little princesses for their hair care appointment. It turns out to be two dogs, which he promptly loses.

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.

Casey finally catches up with the husband who abandoned her, but her rage lessens as he professes his heartfelt remorse at his desperate act. She's understanding to his sad stories of bankruptcy and shame causing him to leave in the first place…until she sees him on his yacht. Meanwhile, Roy teaches Antonio how to dance.

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.

Brian's vow to find a deeper, more meaningful relationship is tested by beautiful but dumb Dani. Meanwhile, Joe tries to deal with the fact that one of his best friends didn't invite him to his wedding.

As a furious storm rages outside, Joe and Helen stop by the "Singles Mingle" to drop off Brian's wallet, intent on leaving as soon as possible to begin celebrating the first anniversary of their wedding. But news soon comes that the roads are closed due to high water and everyone is trapped. Not wanting to let everyone know they are married, for fear of their reaction, Joe asks Helen to be his bride again. Meanwhile, Fay, Roy and Casey mingle, while Antonio is offered his money back and asked to wait in the office till the party is over. And Brian tries to convince the only woman in the place he's attracted to, the sexy bartender, that he's not a pathetic as he seems.

Antonio volunteers to man the Nantucket Suicide Hotline. It soon pays off for him when he scores a date with a caller he helped. When they meet he can't believe his eyes or his luck and keeps waiting for the other shoe to drop—for her to dump him.

When a medical courier leaves his package in the terminal on Halloween Eve, the gang scramble to find him before time runs out.

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.

A financial crisis forces Joe to seek out an investor for Sandpiper. He thinks his luck has changed when businessman Jonathan Clayton comes to the island. But he soon informs them he doesn't invest in companies; he buys them.

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.

Another odd Christmas falls on Nantucket as Antonio drives a nun around in search of a vision she saw in a dream, while Joe plays reluctant host to feuding brothers Lou and Harry, and a little last minute shopping ends up trapping Fay, Helen and Casey.

Roy falls for talk show host Mary Pat Lee, but discovers she used confidential information to ambush Joe and Helen on her show. Meanwhile, Brian pays Casey to run errands for him.

Joe and Helen deal with a crooked vacuum cleaner salesman charging them to repair a vacuum originally sold with an "eternal" guarantee. Meanwhile, Brian gets close to Roy to get closer to his niece.

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.

Brian falls for "R" after reading her love letters mistakenly sent to a former occupant of the house. Meanwhile, Joe and Helen ask Antonio to install a new security system for them.

When Fay goes on vacation, the Hacketts hire a beautiful woman to fill in at the counter. Brian finds her distressingly distracting, while Joe and Helen have uneasy dreams about her. Meanwhile, Casey helps Antonio get a job at the department store, only to see him promoted ahead of her.

Roy invites Joe and Helen over to his house on an important night for him: the introduction of his girlfriend to his mother. But when he's dumped before the fateful evening, Helen reluctantly fills in. Meanwhile, Brian passes on his cold to Casey before her big date.

Brian is surprised to find out his new girlfriend Emily's son is already in college. Further complications ensue when Casey takes a shine to young Shawn. Meanwhile, Joe and Roy go to the circus: Joe to try and deal with his childhood trauma, and Roy to demand an apology from the clown who humilated him in his act.

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.

To cheer up Helen, Joe restores her old cello. While Helen is busy rediscovering her old passion, Joe and Brian discover that the ages-old treasure hunt they undertook when their father died isn't over yet. They and the rest of the gang are led all over New England, only to wind up back at the airport and discover $250,000 in an old suitcase in an airport locker.

Joe and Brian are divided over their new-found inheritance: Joe wants to expand the business, and Brian wants to use the money to leave Nantucket and the tedium of his job. Joe's agony over the dissolving of the partnership is further complicated when he learns of Helen's earth shaking news: she's been invited to study cello in Vienna with the world's greatest cellist. Joe is prepared to sacrifice Sandpiper to help Helen finally live her dream, but it is Brian who makes the final sacrifice by postponing his and Casey's move to the Caribbean in order to run Sandpiper for one year while Joe and Helen are away in Vienna.