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

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 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.

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.

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.

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…

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.

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.

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.

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.

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.

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.

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.

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

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