After spending the night with Helen, Joe thinks they're a couple again. But she goes off to see her boyfriend who proposed to her. So Joe goes after her.

Helen's sister Casey arrives and spoils Joe's dinner plans with Helen.

Brian's going to a psychiatrist to deal with his break up with Alex and is grown dependent on him. Joe and Helen see him and he makes a remark that makes them think they're not suitable for each other. And Lowell is looking for his hat.

After his therapist pronounces him fully recovered from his break-up with Alex, Brian plunges back into the dating world. His efforts at the Club Car yield nothing of interest (despite Antonio's assistance with the "Good Cop, Bad Cop" routine), so he follows the advice of others and starts dating casual friend Joan. That elusive "spark" that is missing from their first three dates finally comes to life when Brian breaks up with her. Meanwhile, Lowell prepares a commencement speech address for his alma mater and Casey has trouble getting a good haircut.

After receiving 20,000 dollars from the family trust fund, Lowell invests the money in an old wax museum. Despite everyone's doubts about it, Lowell renovates the museum, but at the lackluster grand reopening of "Lowell Mather's House O' Wax", he comes to realize it won't be easy. When news comes of a disastrous fire at the museum, Lowell is determined to start again from scratch, but when he realizes that the place is fully insured against fire, he's thankful just to have his money back.

Joe and Helen just want some time alone with one and another, but Brian and Casey continually interrupt them. To apologize, Brian and Casey decide to surprise them with an engagement party, but Antonio misinterprets an overheard conversation and believes Brian to be sleeping with Casey. When she hears about it, Helen drags Joe to the party site well before they are expected.

Cash-strapped Antonio takes a private job driving for a wealthy real estate developer.

Miss Jenkins, the gang's former teacher returns to the island to teach. And the boys had a great crush on her. Brian asks her out and he takes her home and she spends the night. Joe and Helen learn she spent the night. Joe praises Brian till her learns what happened between them. And Roy learns that a guy is dating his mom and wonders why?

Helen's mom comes to the island and she's hoping she'll give her money to help with the wedding as she did with Casey. When she arrives, Casey (who hasn't told her mom that her husband left her) pretends that he is out of town. When she gives Helen the check she's shocked at how little it is. At the same time Brian and Lowell compete to see who can eat more of her food. And Antonio clings to her.

Brian tells Joe they need to drum up more business, and suggests that they hire a celebrity spokesman and the man Brian wants him to consider is Ace Galvin, a former astronaut. Brian brings him over to the island and while trying to schmooze him, he goes around like a wild man which makes Joe wonder if he's the right man. But when it comes time for him to sign, they learn that Roy snatched him. Roy spends his time gloating until he learns of his latest antic.

It's Christmas and everyone has plans: Joe and Helen are going to spend it "together", Casey is going to Boston and sneak into a party, and Antonio is going to "get together" with the woman he's been seeing. Bob, the tower controller, comes to Helen for his usual coffee and jelly donut but Antonio took the last one and Bob freaks out. Antonio tries to offer him another donut but he instead puts a gun on Antonio and demands a jelly donut. While waiting, Bob tells Antonio that things are not good because for one thing his wife is seeing another guy. When Helen makes another donut, Bob comes down but someone eats it. And his wife shows up but it turns out she's the one Antonio has been seeing.

When an old schoolmate comes to the island for a visit, Joe finds himself in wedding hell doing the Hokey-Pokey.

With nothing to do one Saturday night, Joe and Helen start socializing with a new couple on the island, the Tuckers. Joe and Helen's initial trepidation is soon forgotten in all the fun, but the Tuckers quickly tire of their needy counterparts. Joe and Helen soon find themselves dumped and looking for a new couple. 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 Roy flies in a mail-order bride from Russia, Helen tries to convince Roy and Anya that this marriage should never be, but both ignore her. Anya's resolve is weakened with a chance encounter with another man, and the sight of her weeping just moments before their wedding convinces Roy to free her from his commitments to him. Meanwhile, Fay convinces Lowell to pretend to be her lover to impress her soon to be arriving friends, but Lowell insists on cramming and it finally gets to Fay who calls the whole thing off just moments before they are to arrive.

Struggling to agree on wedding plans, Joe and Helen decide to crash another couple's wedding to check out a place. Unfortunately, their fighting infects the newlyweds. Later at the airport, seeing the newlyweds about to take separate honeymoons, Joe and Helen try to right their wrongs and bring the newlyweds back together. Joe and Helen's efforts cause them to see that their wedding plan disagreements are not indicative of the marriage to be, but the two newlyweds are only convinced to get an annulment. Meanwhile, Lowell and Antonio train for a Polar Bears competition.

Past friends and flings return to Nantucket's Sconset High School for a reunion, but someone from the past has a big bombshell that could affect everyone.

Joe finds out some very important news that he's been waiting for. Lowell rethinks his profession and Antonio tries to work up the courage to finally tell Casey his true feelings.

Faye decides it is time to retire.

Brian is asked to appear on a talk show supposedly because he's a hunky guy and he asks everyone to go. And when the show starts he learns that he was tricked to go on the show because they're there to talk about guys who use women and dump them, something he denies until the host reveals the other guest, Brian's ex, Alex. And she goes on about how things were fine between them till they decided to make a commitment which he backed out of. After the show, Alex goes to the island and hashes things out with Brian which ends with them hooking up. And now Brian wants to end it.

Casey discovers Lowell has artistic talents and tries to exploit him. Brian accidentally sends a picture of his penis to Helen's mom.

Brian creates a videotape wedding gift for Joe and Helen, including all the times they spent together.

Carlton's ill health becomes a boon to the gang when Carlton's nephew Lewis invites them over to Carlton's house to start selling off the old man's items. Joe and Helen have an eye for the house itself, Brian drools over a classic muscle car, and Roy looks for furniture. But all is for naught as Carlton's health makes a swift turnaround and, as the doctor sees it, it was hearing all the voices of all the people who came to see him that pulled him through.

With their wedding approaching, Joe tells Helen she's not doing her part like getting their marriage license. She goes to get it and learns that she and Antonio whom she married so that he wouldn't get deported are still married. It seems that someone forgot to submit the divorce papers and that someone is Helen. Now if she files now it will take a month or two for it to be processed and the wedding is a few weeks away. So she turns to Roy who advises her to go to Mexico to get a quickie divorce. She first tries to get Joe out of town so he doesn't find out. She needs Brian to fly her to Mexico. But Antonio first wants to get the marriage annulled. So she and Helen meet with the priest who tries to convince them to reconcile. But when the plane is damaged they try to get Lowell who sick to fix it. And when Joe's departure is delayed Helen tries to keep him from finding out that the airline is closed for the week end among other things.

When Antonio's cousin Dominic and his fiancee 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 his cousin win Teresa back. Meanwhile, Helen's side of the family outshines Joe's when the wedding gifts start to arrive.

Brian throws Joe a bachelor party before his wedding to Helen. Helen thinks it's stupid but let's them do it. But Brian does a bad job at planning it that they end up in a rundown hotel room and the stripper he got is not attractive. While Casey throws Helen a celebration of her own with a male stripper.

It's Joe and Helen's wedding day. Brian and Casey are suppose to help them: Brian's supposed to get the tuxedos and Casey is supposed to help Helen get ready. But because they hooked up the night before, they get up late and scurry to get their tasks done. Brian gets the wrong tuxedos and Casey is so stressed that she messes up Helen's make-up. When Brian gets the tuxedos, he runs into Casey and they do it again and he throws them into a laundry cart and they're taken away. Antonio, who was hoping to tell Casey how he feels about her, upon learning what happened between her and Brian attacks him and knocks the wedding ring into the toilet. Joe tries to get it but gets stuck.