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

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 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.

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.

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.

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.

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 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.

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.

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.

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.

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.

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'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.