When Helen has another audition and is not chosen; Brian points out that she dresses too conservatively and that she should consider sexing it up a little. Meanwhile, Fay is attracted to a man who has been traveling around the world and is on the last leg of his journey. When Fay asks him why doesn't he complete it, he claims that if he does he will die.
A pilot who knows Brian has a layover at Nantucket and tells him that his ex-wife, Carlo, is moving to London. Brian learns that she'll have a layover in Boston so sends her a message asking her to meet him. When Joe learns of this he tells Brian she won't be there. But Brian decides to go even with a fog covering the island. Joe and Helen decide to follow him.
Brian asks a girl out and she agrees on the condition that he find someone for her friend Cindy. And he volunteers Joe. Joe initially refuses but Brian guilts him into it. Later he learns that Cindy is very "popular", which makes him reconsider, but then Helen guilts him. And at their date one of her exes shows up and when he treats her crudely Joe stands up for her.
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.
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.
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 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.