Trying to get Helen to change her policy about dating pilots, Brian hires an actor to pretend to be a pilot but who shares the same interests that Helen has. It isn't long before they're dating. But things go awry when the guy really falls for Helen and she makes some decisions that will greatly affect her life.

A reporter comes to Nantucket to do a story on Joe. But when he talks to Brian and hears some of his stories, he decides to interview him. And Joe is upset.

When a conductor comes to the island, Helen tries to talk to the man and maybe play for him but she freezes. Brian comes up with the plan to hold to one of his baggage. Helen then goes to where he is staying to return it and play for him. And he tells her that she's no good. That's when Joe goes to see the man and tell him off.

Roy invites himself into the group's social circle.

A guy calls Joe, telling him they were close years ago. But Joe doesn't remember him. But when Joe meets him and asks him to be his best man at his wedding Joe can't refuse. Things get weird with the wedding approaching.

Joe and Brian compete to see who get Helen the better birthday gift as a means to try and impress her.

After getting Joe out of many unpaid parking tickets by flirting with the police officer, Brian soon learns she isn't his type. Lowell keeps a video camera handy in case something funny happens.

Joe gets grounded by the Doctor for his high blood pressure, so he takes his frustration and anger out on Brian, who soon quits to enroll at TWA flight school. Joe, now searching for a new pilot, is unable to find anyone who will work for the salary he is offering. So he decides to sell Sandpiper to Roy. That is, before Brian returns and convinces him to stay in business.

Due to desperation and loneliness, Joe and Helen decide to go on a date. To spare his feelings, they choose to keep it a secret from Brian.

Roy gets the surprise of his life when he agrees to let his star athlete son take cello lessons from Helen.

After everybody's holiday plans fall through, they decide to surprise Faye at her Christmas party. When they arrive, they discover she'd lied about her plans and find her all alone.

Helen decides to take flying lessons from Joe but his classes are too long and boring so Brian offers to let her fly the plane. Shortly after, Brian is injured and Helen finds herself behind the controls.

Joe is torn, on one hand he promised to take care of Helen, who is gonna be laid up for the night after visiting the dentist. And on the hand he's missing the biggest College Basketball game of the year, when Providence plays Boston College. Joe soon finds out Helen's TV is in the shop, so he bundles up unconscious Helen and takes her to his house and the party. She wanders off and everyone except Roy has to go looking for her.

For the upcoming model show, Lowell brings in his most prized possession, his radio controlled Graf Zeppelin model. Storing it in Joe's office he makes only one request, that no one touch it, including Joe. But Joe can't resist and of course destroys it, after Roy bursts in without knocking and crushes it behind the door. Meanwhile, Brian's attempt at cheering Fay up by letting her beat him in a game of tennis, turns into embarrassment as the news of the victory spreads. So Brian, with wounded pride, challenges Fay to a rematch, but bows out when he realizes that he can't beat her. So he fakes an injury to save face. Helen confronts Roy about not hiring any female pilots, so he claims that a male looking pilot is actually female.

When Joe's back goes out and forces him into a stay at the hospital, Brian takes over Sandpiper. His eagerness is soon deflated, when all his new ideas and crazy promotions turns into a disastrous mess. When Joe returns he finds the Airport in complete chaos, with the Marching band and the team mascot ready to board the plane for a world record attempt, and Brian looking for the plane after it went 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 a report, which catches the notice of an eccentric group of UFO enthusiasts.

Valentine's Day gets off to a rocky start for Helen and Joe. Joe's gift of chocolates is not appreciated by the once-overweight Helen. Helen apologizes for taking it the wrong way, sending Joe a note telling him to meet her at their "special place" later that night. However, they have different places in mind -- for Joe, it's Indian Point, where they had their first date. For Helen, it's Pontorelli's, where they first ate. After a confusing night, they finally end up at Pontorelli's for a late Valentine's Day. 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.

Wanting a night alone, Joe and Helen kick Brian out of the house, but Brian shows up the next day with a woman named Gwen who he intends to marry. Despite the objections of Joe and Helen, the happy couple and the wedding party (with Roy as the minister and Joe and Helen as the Best Man and Brides Maid, respectively) go up in Joe's plane, to watch the marriage ceremony and subsequent skydive. In the midst of all this excitement Joe and Helen decide to take the plunge too. Suddenly Gwen has a major change of heart and she and Brian decide not to get married after all, as do Joe and Helen.

When Brian starts to date Kenny's mother, Kenny is worried about Brian's reputation with women. But just as Kenny warms to the idea of them dating, Brian dumps her. Meanwhile, Joe and Helen squabble over the issue of privacy.

Joe and Brian's mother who left them, comes back. While Brian is happy to see her, Joe isn't. And things get worse when she tells them why she chose not to return.

Brian is forced to live with Faye for a week and jumps to conclusions when he thinks he sees her on a fugitive TV show.

Much to Joe's surprise, Helen wins a job with the Maine State Symphony. But when Helen comes to Joe and tells him she would stay if he only asked, the discussion turns into a huge fight. Then comes the unwelcome news that the Symphony has lost their funding and there is no job. Joe prepares to apologize but Helen's ready to leave; tired of not getting anywhere with her musical career, she decides to leave Nantucket for New York City. Meanwhile, a confused looking woman who doesn't speak english and has been hanging around the airport gains Fay's sympathy and Roy's hostility.