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.

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.

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.

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.

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.

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 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.

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.

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.

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.