Joe and Helen go on their first date and Brian hires high school student Kenny McElvey as a backup pilot for the grounded Joe.

Brian is ecstatic when he and Joe's mother returns to Nantucket years after deserting them and their father. For Joe, it's too little too late, because he can't forgive her for leaving.

The arrival of Millionaire Mimsy Borogroves has Fay, Roy and Helen eager to tap into her wealth. But Mimsy has eyes for Brian, and he soon enjoys the good life, receiving expensive presents and accompanying Mimsy everywhere, much to Joe's disgust.

Joe and Brian learn their childhood home has been condemned due to storm damage and all efforts to save it fail. The gang visits one last time before the wrecking ball flies, and they relive some childhood memories.

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.

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.

Joe and Brian, in heated competition, pull out all the stops in a transparent attempt to get closer to Alex.

Brian's exclusive commitment to Alex is sorely tested when Joe flies in a group of models for a photo shoot. Helen's decision to name food items on her menu after the people in the airport doesn't go as well as she hoped.

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.

To counteract Roy's Aeromass promotions, the Hacketts woo famous astronaut Ace Galvin as a celebrity spokeman for Sandpiper. Joe and Brian soon discover that Ace is as charming and persuasive in public as he is irratating and annoying in private life. Any hopes of signing him up are dashed when Roy beats them to the punch, but Roy quickly discovers just how obnoxious Galvin can be.

Carlton's ill health becomes a boon to the gang when Carlton's nephew Lewis invites them over to Carlton's house to start selling off the old man's items. Joe and Helen have an eye for the house itself; Brian drools over a classic muscle car; and Roy looks for furniture. But all is for naught as Carlton's health makes a swift turnaround.