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

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.

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.

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.

After Brian's depression over Alex's departure results in a near break-down during a flight, Joe suggests he go see a psychiatrist. Once there Brian makes a partial recovery, but Joe is the one with the true breakthrough, as he realizes that his earlier acceptance of Helen's suggestion of an earlier wedding date may result in trouble for him in the marriage. When confronted, Helen agrees on the original wedding date, until Casey sparks some doubts. Misunderstandings ensue, resulting in the wedding being called off. Meanwhile, Lowell attempts to find a hat that Antonio lost.

With nothing to do one Saturday night, Joe and Helen start socializing with a new couple on the island, the Tuckers. Their initial trepidation is soon forgotten in all the fun, but the Tuckers quickly tire of their needy counterparts.

Meanwhile, Brian and Casey start hitting the singles hangouts together and Antonio becomes Lowell's "hands" when Lowell injures his working on the cab.

When Antonio's cousin Dominic and his fiancée Teresa visit Nantucket, Antonio finds himself struggling to ignore his feelings for Teresa. He succumbs to temptation during supper at his apartment, after Teresa voices concerns over problems with her relationship, but he ultimately helps Dominic win her back.

Meanwhile, Helen's side of the family outshines Joe's when the wedding gifts start to arrive.

The sad news of Harrison Kingsbury's death in Miami is occasion for celebration at Sandpiper, as Kingsbury's oldest daughter hires the Hacketts to bring the body back to Nantucket for the memorial. But the brothers fly the wrong body back to the island, and it's up to Joe to impersonate the late Kingsbury at the funeral.

Back from vacation, Lowell goes out for a meal of hot wings with Antonio and lands in hot water when he witnesses a mob hit. After he is threatened by the gangster's lawyer, he decides to join the Witness Protection Program and leave Nantucket forever, rather than see the gangster released and have a chance to kill again.

When news arrives that Davis Lynch has re-surfaced, Helen recounts the tale of how she never broke off her engagement with him, then tries to break the news to Davis, while not alerting Joe.

The contractor Joe and Helen hires to build their new house falls apart when his wife kicks him out, and the Hacketts try to rebuild his confidence and get him back to work.

Meanwhile, a vacationing George Kennedy is bothered by an annoying fan: Brian.

Brian's vow to find a deeper, more meaningful relationship is tested by beautiful but dumb Dani.

Meanwhile, Joe tries to deal with the fact that one of his best friends didn't invite him to his wedding.