The arrival on Nantucket of beautiful new helicopter pilot, Alex Lambert, soon has the brothers chasing after her, despite her obvious non-interest. Meanwhile, Antonio gets invited to the Tuesday night rat shoot with Lowell and his buddies Tom and Tucker, where he upstages Lowell by shooting more rats.

Alex agrees to a date with Brian at the Parade of Tall Ships. Brian borrows Lowell's boat for the event. But Brian sinks Lowell's boat. Joe and Brian are then forced into inviting Lowell to stay with them for a while and are surprised at how well Lowell cooks and how eager he is to do the household chores. They enjoy his visit so much that when his insurance check arrives they decide to hang onto it for a little while. But soon the honeymoon comes to an end as Lowell's strict discipline rubs the Hackett's the wrong way. But when they've agreed to boot Lowell out they discover his check is missing. At supper that night, he confronts them with the check. While ironing out the misunderstanding about the check, the brothers and Lowell make peace and they invite him to stay on.

Rumors abound at the airport when Antonio reveals he saw Joe's car parked outside of Alex's apartment late the night before. Soon the airport - especially Brian and Helen - is buzzing about the possibilities. Since Alex had been intoxicated that night, Joe is the only one who knows the real truth and he won't tell. Alex then makes a big scene and pretends to leave after he won't tell even her. But she soon returns, and he eventually tells her the whole story. They share a steamy kiss.

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.

Loose talk at Helen's house one night between Antonio,Helen and Alex reveals Alex once posed for Playboy. Helen and Antonio promise to keep it a secret,but at the airport the following Monday,Joe and Brian quickly find out about it. They then quickly raid Roy's office and his collection of Playboys, eventually finding the photo. Antonio becomes the focus of Alex's wrath, but it is soon revealed the secret was leaked by a subconsciously jealous Helen at the beauty parlor. Angry Words are exchanged between Alex and Helen when the truth comes to light. The situation is diffused by a very anxious Fay, who wants to use the bathroom and can't while they are arguing.

Hoping to impress Alex, Brian claims to know Clint Black. So they go to Boston where he has a show and they go to his hotel room and that's when things get complicated.

In their pursuit of Alex,Joe and Brian take some indirect tips from Helena as she describes her own reactions to another's man advances. But Alex sees through all their ploys, until Joe and Brian finally resort to honest conversation over dinner to settle their relationship with Alex.

Weeb Gilroy's death has Lowell searching for the right words to write for a eulogy for his long time friend. Words fail him at the end; all he can think of is to finish working on.

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 setup.

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.

After spending the night with Helen, Joe thinks they're a couple again. But she goes off to see her boyfriend who proposed to her. So Joe goes after her.

Brian is asked to appear on a talk show supposedly because he's a hunky guy and he asks everyone to go. And when the show starts he learns that he was tricked to go on the show because they're there to talk about guys who use women and dump them, something he denies until the host reveals the other guest, Brian's ex, Alex. And she goes on about how things were fine between them till they decided to make a commitment which he backed out of. After the show, Alex goes to the island and hashes things out with Brian which ends with them hooking up. And now Brian wants to end it.

Brian creates a videotape wedding gift for Joe and Helen, including all the times they spent together.

Brian is asked to appear on a talk show supposedly because he's a hunky guy and he asks everyone to go. And when the show starts he learns that he was tricked to go on the show because they're there to talk about guys who use women and dump them, something he denies until the host reveals the other guest, Brian's ex, Alex. And she goes on about how things were fine between them till they decided to make a commitment which he backed out of. After the show, Alex goes to the island and hashes things out with Brian which ends with them hooking up. And now Brian wants to end it.

In their pursuit of Alex,Joe and Brian take some indirect tips from Helena as she describes her own reactions to another's man advances. But Alex sees through all their ploys, until Joe and Brian finally resort to honest conversation over dinner to settle their relationship with Alex.

The arrival on Nantucket of beautiful new helicopter pilot, Alex Lambert, soon has the brothers chasing after her, despite her obvious non-interest. Meanwhile, Antonio gets invited to the Tuesday night rat shoot with Lowell and his buddies Tom and Tucker, where he upstages Lowell by shooting more rats.

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.

Rumors abound at the airport when Antonio reveals he saw Joe's car parked outside of Alex's apartment late the night before. Soon the airport - especially Brian and Helen - is buzzing about the possibilities. Since Alex had been intoxicated that night, Joe is the only one who knows the real truth and he won't tell. Alex then makes a big scene and pretends to leave after he won't tell even her. But she soon returns, and he eventually tells her the whole story. They share a steamy kiss.

Loose talk at Helen's house one night between Antonio,Helen and Alex reveals Alex once posed for Playboy. Helen and Antonio promise to keep it a secret,but at the airport the following Monday,Joe and Brian quickly find out about it. They then quickly raid Roy's office and his collection of Playboys, eventually finding the photo. Antonio becomes the focus of Alex's wrath, but it is soon revealed the secret was leaked by a subconsciously jealous Helen at the beauty parlor. Angry Words are exchanged between Alex and Helen when the truth comes to light. The situation is diffused by a very anxious Fay, who wants to use the bathroom and can't while they are arguing.