Lyle, a man Fay met while on vacation comes to the island to court her. He proposes to her and they were in the process of getting married when the minister utters his full name. That's when Fay freaks out, because he has the same name as her other dead husbands. She then goes to Joe who is nursing a cold to ask him what she should do.
Joe and Brian decide to go to a hockey game in Boston. They ask Antonio to man the counter. He gives the last seat to an old woman. And then a guy who says he was booked to go o the flight arrives. But because he was late Antonio gave sway the last seat. He says that he will regret it. Joe and Brian return and say the game was disappointing because the star player wasn't there. And Antonio tells them about the guy and they learn it was the hockey player. He later goes on the air and blames Sandpiper for his missing the game. And that's when they're the most hated ...
Helen learns that her ex boyfriend Davis has been detained in Asia for over a year and is now on his way back to see her. She then tells Joe to go to Boston to get something. The guys are wondering what's up with Helen. She tells them that she didn't break up with him when she accepted Joe's proposal. She tells them that on the night she was going to see Davis, Joe proposed to her and she accepted. She told Joe that she has to see him alone but when she sees him, he surprises her with a surprise engagement party. And before she could tell Davis she accepted Joe's ...
When Joe learns that Sandy Cooper, the woman he says is obsessed with him, is coming he freaks out. Helen thinks he's out of his mind. And when she arrives, she's there for Brian. Joe goes on of how demented she is, Helen takes him to a therapist. But during one of his sessions Sandy shows up claiming to be his wife.
After a chance encounter, Antonio searches for the girl he shared a moment with in the airport. He enlists everyone's help to try to find her. Brian and Helen size up women at the ticket counters for emotional baggage that they might carry.
Joe finds the time capsule, he, Brian, Helen and Casey buried when they were kids. Inside are letters that they wrote what they thought they would be in the future. So they each read their letter, Joe thought he would be baseball star, Brian thought he would be a spy, Casey thought she would be a supermodel. And they thought Helen would still be the fat girl And Helen is a musician.
Joe and Brian learn that a woman whom they know is an exotic dancer and will be performing for the last time so they decide to go. But Joe has to find a way not to tell Helen. But when she asks him where he is going, he makes up a story of volunteering at a retirement home. And in order to be able to look her in the eye he goes to the home.
Joe, Helen, Brian, and Casey are fed up with their living arrangements, and Joe's "big board"; however, Felix the Contractor says the sinkhole on Joe and Helen's plot isn't the only delay in building their new house. Joe shows Helen the house of their dreams; but what to do with their poured foundation? In the meantime, Antonio gets $1000 from his taxes and decides he is going to spend it all on himself. Unfortunately, a broken tooth leads to a series of unfortunate events that whittles his check down. It all ends in fire and chaos, reminiscent of... last year.
Brian and Casey burn down Helen's house, Joe and Helen burn down Brian's house. This is too much of a coincidence for the insurance company. Joe, Brian, Helen, and Casey must sweat it out with the insurance adjuster before Antonio shows her passion can ignite a flame.
Antonio works a suicide hotline one night and finds himself on a date with a depressed caller. When she turns out to be gorgeous he wonders how long until he gets dumped. Helen has to compete with a sandwhich vendor cart.
It's Halloween and everybody wants to enjoy it and go to parties. But a guy shows up and buys a ticket; Joe and Brian don't want to fly him cause they have plans. The guy gets a call from his wife who had earlier dumped him. He says that he's a medical courier and he is carrying the gift of life. But Joe and Brian convince him to go to his wife and he leaves his cooler behind. They look inside and see a canister that says Nelson's heart. They assume it's a heart for a transplant. So they try to find out where it goes.
Casey encourages Brian to use his insurance money to open a martini bar. Things go awry when the first customer through the door slips and falls. Brian's problems are compounded when he learns Casey never got insurance. Roy and Faye hunt for ET's.