Roy reveals his wife Sylvia is not dead after all, but living in Boston after having deserted him abruptly sixteen years ago. Accompanied by Brian, Roy flies to Boston to win his wife back, only to find her life has taken a surprising turn without him.

Stunned by the news that their "quickie" divorce won't be for another three years, Helen sadly resigns herself to life as Antonio's wife. But she gains new hope when Brian tells her about a green card lottery.

To help commemorate the anticipated breaking of Joe's old high school strike-out record, Joe's old coach coerces him to fly him and his star player to the game. But when heavy fog prevents his landing on time, some question whether his concern was safety or for his own high school record.

Roy is struck out at Fenway Park by his own rendition of the National Anthem, and Fay commits a costly personal foul at work.

Antonio performs his civic duty when he helps bring to court a suspected robber and then testifies against him. But then the suspect gets released on a technicality, and Antonio starts to fear for his life.

Alex finally agrees to a date with Brian, only to find out later it was all a set-up.

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

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.

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.

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 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.

The arrival of Helen's elder sister Casey to Nantucket sidetracks Joe's plan to give Helen an engagement ring. What was originally planned to be an evening for two at Lexington's becomes a party of four, with Casey along to catch up with Helen and Brian along to occupy Casey. Then, before Joe can give Helen his ring, Casey gives Helen an even bigger ring as a gift, and Joe's angry frustration brings the night to a halt. He apologizes later that night and gives her the ring, but once again Casey drops in to spoil things. Helen finally stands up to Casey, who then reveals that her husband has left her, and she has no where to go. So Helen invites her to stay with her for as long as she wants.

To pay off a $1500 IRS fine, Antonio becomes the driver/errand boy/personal assistant to Gavin Rutledge, a businessman visiting Nantucket for a week for a real estate deal. Uncomfortable at seeing Gavin dating Casey, Antonio faces a major dilemma when he finds out Gavin is married. At the cost of his job, Antonio tells Casey about Gavin, and Casey shows her gratitude by giving Antonio a jewelry gift she received from Gavin.

Meanwhile, Joe is Irked that Brian had an erotic dream about Helen.

After receiving the news that he might be the father of Sara's little boy, Jason, Joe is advised by Roy to keep quiet on the whole affair, but Joe's guilt forces him to tell Joe and Helen.

Meanwhile, Lowell questions his choice in careers and Antonio struggles to make Casey his valentine.

As the wedding draws near, Brian struggles to come up with a gift idea for Joe and Helen. He finally hits on the idea of making a video for them, and goes about capturing everyone's memories of their relationship on video.