When news arrives that Sandy Cooper is returning to Nantucket, Joe fears her high school obsession with him will return but the others think he's imagining things. Meanwhile, Antonio tries to raise money to send to his family and Roy is worried about a visit from his cranky mother.

Joe feels the weight of the world coming down on him as everyone comes to him to help solve their problems. As the stress mounts, he knows he must make a drastic change.

While trying to create a perfect evening with her boyfriend, Davis, Helen runs into obstacle after obstacle with various friends who assist in aiding with what can only be certain disaster.

With Joe MIA, the burden of running Sandpiper Air falls all on Brian. As he struggles to keep things in the air, he gets a clue to where Joe ran off to.

To help pay for his new used cab, Antonio gets a job as a chauffeur for Carlton Blanchard. Things get even worse when Carlton's equally annoying nephew, Lewis, arrives on Nantucket to attend Carlton's banquet.

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.

Joe may have finally found a bank willing to float him a loan to expand Sandpiper Air. Helen anxiously awaits Davis' mid-week arrival, sure that he's coming to break up with her.

Roy gets bored and decides to have some fun at everyone else's expense.

Joe, Brian, Helen, and Lowell head to Boston for a night on the town but end up at a party that's more than what it seems. Roy, Fay and Antonio pool their resources to win a radio contest.

Davis finally shows up to see Helen after a string of cancellations. A furtive search through his luggage reveals a gift that may be inappropriate at this stage of their relationship. Fay rescues a lab rat from her experiments by her psychology professor, risking a bad grade and charges of theft.

To Helen's disgust and Brian's envy, Joe starts dating a 19-year-old co-ed. Roy and Antonio find a dog whose cute charm no woman can resist.

When Joe flies in a potential investor, he's more interested in Helen than Joe's airline.

Lowell's ex-wife arrives on Nantucket for a friend's wedding. Brian faces the prospect of meeting Alex's parents. Joe deals with the loss of a tree and Fay becomes overbearing as Helen organizes a holiday party for children.

Tired of Lowell's strictness, the brother's boot him out of the house. Despite his reluctance, Lowell buys a new house and tries to adjust to the experience of living alone for the first time.

Davis cancels yet another date leading Helen to accept a date with another man. As for Joe, after two dates conflict, he tells a lie to get out of one of them only to have the other one cancel.

Somebody is asking questions around the island in search of Fay and she's spooked. Antonio loves the new cable TV service that Roy's shady friend installed.

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.

To ease Alex's embarrassment over having to take a job as a waitress at a medieval themed restaurant during the off-season, the gang tell their own stories of embarrassing off-season jobs.

Roy's ex-wife makes a surprise appearance on the island. She seems to be up for a reconciliation, much to Roy's delight, but may have ulterior motives. Helen tries to fend off a smitten and slightly crazy waiter from the crab house she went to the other night.

Lowell and Bunny make their separation final by signing the divorce papers only to start sleeping together again. Meanwhile, Antonio consoles a woman who's cheating husband left his cellphone in Antonio's cab.

Joe is upset at playing chauffeur to the other couples for their romantic trips off the island but it's everybody else who ends up suffering. Meanwhile, Antonio and Fay help Roy change his image to try to impress a new woman.

Everyone is of course skeptical when Brian announces that his relationship with Alex is special. To try to insure that their relationship lasts longer than a couple of weeks, they decide not to sleep with one another yet.

Brian moves in with Alex, and both quickly become irritated by the other's annoying habits. Meanwhile, Lowell attempts to come up with a name for his sister's baby.

When Brian's old friend shows up and they resume their wild, partying lifestyle every night, Alex grows increasingly neglected. Lowell takes in his idol, over-the-hill television superhero Big Strong Man, who takes advantage of his hospitality.