When Sandy Cooper returns to the island, Joe fears yet another bizarre encounter with the obsessed woman. She tells him it was all a practical joke and he believes her until a stop at Helen's house becomes Sandy and Joe's wedding day. Meanwhile, Fay forces the old 70's wardrobe, of one of her dead husband's, onto Antonio and he wears it to make her feel better, despite hating it. Also Lowell tries life as a vegetarian.
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.
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 ...
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...
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 ...
When digging through the rubble of Helen's home, Brian and Casey unearth a suitcase and photograph that had been the Hackett brother's only inheritance from their late father. Brian's attempts to remind Joe of that fails, but Joe later sees a vision of his late father and forgives Brian. Meanwhile, Antonio takes his revenge on Brian and Casey and Helen takes out her anger on Casey's clothes.
A member of a wealthy family hires Joe and Brian to go to Miami to pick up the remains of the family patriarch, who died there. But because they drank a lot the night before they left, Joe got the wrong casket. So now they try to get the right one but there's going to be a viewing so what are they to do. Brian decides to let Joe take the dead man's place till the body arrives. And while waiting he learns all sorts of things about the man and his family.
Lowell witness a crime. The perp then tries to get him not to testify. The Feds then offer to place him in the Witness Protection Program but when he learns that if he does, he will no longer be able to see his friends. So he asks Joe what he should do but Joe tries to give him advice but tells him ultimately it's his decision.
When the insurance company gives Helen a big check for what she lost in the fire she goes on a shopping spree. Casey refuses to have sex with Brian unless they can find something they share in common. Antonio depressed at his (lack of a) love life decides to go back to his ex who is hideous.
When Brian starts eating incessantly and his work is affected, Joe tells him to get his act together. Helen tells him that he needs to go to her overeaters support group and when Brian goes to talk he reveals why he is eating so much. Antonio buys a pair of expensive shoes that are a little tight and he says he just has to break them in but it appears his feet are the ones that will break. Casey goes to interview for a job and pretends to be a fan of the Three Stooges which the man interviewing her is.
It's Christmas. Joe wants to bring Helen to Vermont but Helen wants to throw a traditional Christmas party. Joe agrees on the condition that as soon as it's over they go to Vermont. So Helen invites everyone and Brian tells Casey he's bringing a date because of what happened between them. She tells him she's also bringing a date, only it's a lie. She tries to find someone and picks Lewis. Things go bad when Joe learns that the road to Vermont will be closed in a few hours so he tries to rush the party. Antonio brings gifts for everyone, but they don't reciprocate so ...