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.

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.

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 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.

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 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.

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.

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.

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.

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

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

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

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

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.

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.

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.

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.

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.

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.

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.

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

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.

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.

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.