In order to get Helen to break her vow that she does not date pilots, Brian hires an actor to play the role of a charming pilot to ask out Helen.

A magazine writer wants to do a cover story on Joe but finds Brian's life much more interesting. Cliff Clavin and Norm Peterson visit the island.

Helen plays her cello for a very famous conductor visiting the island on his honeymoon. Meanwhile, Fay prepares for a role at a carnival by predicting the future reading tarot cards.

Fay keeps inviting Roy to group events despite how much the group dislikes him. Roy asks for help from Joe on how to be a nice guy and tries to make friends with the gang by joining them in a friendly game of Trivial Pursuit. Unfortunately, Lowell is his partner.

Joe feels obligated to hold a bachelor party for a guy he can't remember going to high school with but the guy considers Joe his best friend. Lowell is fascinated by a metal plate in Roy's head.

Joe and Brian compete to get Helen the better birthday gift as a means to impress her. Fay creates a budget for Lowell and learns that he's still paying for a tuxedo he rented years ago.

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 "America's Wackiest Videos" TV show.

Joe is grounded due to hypertension forcing Brian to take every flight. Joe is unable to find a new pilot willing to work for what he can afford to pay leaving Joe to consider selling Sandpiper.

Joe and Helen attempt to secretively go on their first date. Brian hires a backup pilot for the grounded Joe.

Roy's son R.J. takes cello lessons from Helen. Roy agrees to pay for the lessons after he thinks R.J. is "hot for teacher." Helen convinces R.J. to divulge a secret that he is agonizing over telling his father.

After all their plans for Christmas go badly, the gang tries to cheer Fay up who is having her first Christmas without her husband.

Helen is bitten by the flying bug after Brian lets her take the plane's controls for a few minutes. She decides to take flying lessons from Joe but his classes are too long and boring so Brian offers to take her up again. They experience some turbulence and Helen finds herself at the controls but never learned how to land.

Joe has to take care of Helen when she gets her wisdom teeth pulled out. Unfortunately for Joe, her appointment falls on the same day as a party to watch the biggest college basketball game of the year between Boston College and Providence. With Helen's TV in the shop, Joe's loyalty is tested.

Brian is upset because Fay beat him at tennis. Meanwhile, Roy tries to mess with Helen's mind by claiming that one of his male pilots is actually female and Joe, despite being told otherwise, can't resist flying Lowell's prized Graf Zeppelin model he's keeping in Joe's office ahead of a model airplane show.

Joe is hospitalized for back trouble and leaves his normally overly detailed schedule for Brian to manage Sandpiper. Brian disregards Joe's schedule and runs the airline his own way. All his schemes suddenly go off the rails when the plane goes missing.

Joe and Brian think they see a UFO. Joe is hesitant to file an FAA report, fearing that Sandpiper Air will be blacklisted. Brian goes ahead and files the report which catches the notice of an eccentric group of UFO enthusiasts. Meanwhile, Helen informs Fay she still owes her money on her lunch tab but Fay insists she paid it.

After a disastrous start to Valentine's Day, Joe and Helen agree to meet at their special place. Unfortunately, they each have a different idea as to where that is. Roy's blind date exceeds all his low expectations but all he can do is try and figure out what's wrong with her.

Wanting a night alone, Joe and Helen kick Brian out of the house. Brian shows up the next day with an adventurous, globetrotting woman whom he intends to marry.

Brian demonstrates to young pilot Kenny how he is so successful with women. However, when Kenny learns that Brian asked out his mother, he is less than thrilled knowing of Brian's history. Meanwhile, Joe and Helen squabble over the issue of privacy in their relationship.

The brothers' estranged mother returns to Nantucket after Brian sees her at a sporting event on TV. Brian is thrilled but Joe feigns apathy to hide his anger for having to be the responsible one of the Hackett household.

While the brothers' house is being fumigated, Brian sees a woman who looks like Fay on a TV show about escaped fugitives. He's convinced Fay is the killer and is trying to murder him.

Helen gets a music job with the Maine Symphony Orchestra forcing her and Joe to talk about their future. Meanwhile, a confused woman who doesn't speak English has been hanging around the airport and gains Fay's sympathy and Roy's hostility.