When Ally has to do a school project on genealogy and interview her oldest living relative, Ray helps her track down his father Frank's long-lost Aunt Sarina in Italy, and they decide to write her a letter. Things get interesting when Aunt Sarina takes the letter and the "stop by if you if you're ever in America" literally.
After Ray asks Debra why she ever married him, they take a walk back in time to the very beginning of it all. Ray is very nervous, he's about to propose to his lovely girlfriend Debra, and nothing is going right. When he finally pops the big question, she accepts, the families celebrates, and all is well, for about five minutes.
After Raymond begrudgingly agrees to be the auctioneer at the Our Lady of Faith School auction, he’s pleasantly surprised with the laughs he gets at Debra’s expense. Debra tells him that she’s going to get even, but later retracts her warning, but it’s too late, Ray is convinced that Debra is plotting her revenge.
When Marie discovers that Ray held an unchaperoned party at their home some 20 years ago, she is hurt and disappointed that her favourite son lied to her. Unable to forgive or forget, Marie can no longer put Ray on a pedestal, and he’s been bumped for big brother Robert, and it’s killing the needy Raymond.
Robert’s entire demeanour changes when he starts clubbing with his patrol partner, Judy, and her friends. When he starts using expressions such as “this is so whack” and “I’m down with it,” and showing up in mustard coloured suits, the Barone family find it hard to believe how much Robert is changing in order to fit in with his new friends.
Just as Frank and Marie are about to embark on a Caribbean cruise, Frank hurts his knee and can't go. Ray, not wanting to disappoint his mother, accompanies her on the cruise. Marie is having the time of her life soaking every ounce of fun in the sun, while back home, Robert is just about out of patience being the caretaker for the injured Frank.
When Robert and Amy have sex in Robert's apartment, they forgot to close the curtains. It doesn't take long for the other tenants to launch a partition to make curtains mandatory. Humiliated, the loving couple are desperate to find a new make-out spot. Debra wants Ray to help them, so he offers Robert and Amy the Barone household basement.
After Frank stops by Ray and Debra's house to borrow some ointment for his thighs, he becomes unusually interested in spending time with Ray. Initially, Ray finds it weird and is concerned that his father has suffered a physical trauma to the head, but after two of Frank's friends from the lodge stop by, all becomes clear.
Ray and Debra are discouraged when they realize that their sex life isn't what it used to be. They reassuring each other that it's not an unusual occurrence for older couples to experience since the kids are always underfoot, they're sleep deprived, etc. Trying to make themselves feel better, they approach Frank and Marie asking them what constitutes a "normal" sex life for an older couple.
Ray and Debra are drafting their wills and must decide who would make the best guardians for their children. After pondering long and hard over their options, Ray and Debra choose the two people who they feel would be the best candidates to raise their children, should anything happen to them. But their choice doesn't meet with everyone's approval.
Ray is bewildered, but not altogether displeased when Debra starts initiating sex on a more than regular basis. He can't believe his luck, he is even willing to give up his golf game to satiate Debra's newfound desires. But he can't leave well enough alone, and decides to look into the reason behind his wife's sudden burst of energy.
Inspired by how well the Barones got along at the Thanksgiving dinner, Debra is intent on finding a way to improve her relationship with Marie, and decides to spend a whole day cooking with her. Meanwhile, Ray gets roped into having Frank and Robert accompany him to a car show, where he has his own method of getting along with his family.
Ray and Debra have differing points of view on how best to handle the situation, when they learn that Ally has been bullying another child on the school bus. Ray thinks Ally's pushiness comes from Debra, and she thinks that if she doesn't instil independence in Ally, she'll end up being a wuss, just like her Raymond.
Everyone gets on Ray's case because he's doesn't go to Sunday Mass. When Ray starts feeling guilty and sees the good example his father Frank is setting by attending church, he commits to becoming a regular parishioner. But when he shows up at the church, he soon figures out the real reason his father likes attending Mass.
On the 10th. anniversary of their wedding, Ray and Debra sit down in the living room to watch their wedding video, but the romantic evening soon turns sour when the wedding video has been recorded over. Instead of a wedding, they are watching the 1991 Super Bowl. Debra gets really angry at Ray, and their marriage looks to be in serious trouble.
Ray screws up a Hackidu trade for his daughter by refusing to trade several cards for one Scramisaur card, which is rare and worth a lot of money. Ray thinks he's being the perfect father by taking an interest in Ally's Hackidu hobby, and advising her on the card swap, but she is disappointed as the Scramisaur is not only rare and valuable, but also her favourite Hackidu.
When Debra realizes that all her time is spent with the kids, Ray, and his family, she tells Ray to take the kids out more often so that she can have more time to herself. Ray doesn't understand why Debra needs more time to herself, and when Marie hears about it, she starts thinking that something is wrong with their marriage, and when Ray finds out what his wife is doing with her alone time, he starts to get worried.
Still recuperating from his recent run-in with a bull, a cantankerous Robert is driving everyone crazy with his mean-spirited behaviour. When his doctor tells him that he needs two more weeks of of recovery, which means two more weeks at his parents' house, his attitude worsens. But Debra things that there is another reason for Robert's bad attitude.
When Ray witnesses Debra's hypersensitive mood and generally annoyed reaction to everything he says and does, he checks the calendar and realizes it's going to be a long couple of days ahead. In his desperate attempt for a "quick fix," he makes a bad situation worse by suggesting that a simple pill will help with his wife's insufferable mood swings.
When Marie surprises the family with the news that she's treating them all to a two-week vacation in Rome. Everybody loves the idea except Raymond. It's virtually impossible not to enjoy oneself in a country as beautiful as Italy, but if anyone can manage it, Raymond can. Not willing to let his sour mood spoil it for the rest of the family, Debra, Frank, Marie, Robert and the kids go on their merry way and soak up the atmosphere, sights, smells and tastes of the city of love and try their best to ignore Ray. Meanwhile, Robert meets the girl of his dreams. She's stunningly beautiful, unbelievably sexy and works in a gelato shop.
Robert finds himself in the most unlikely position of having to choose between his girlfriend Amy, ex-wife Joanne, or Italian summer love, Stefánia. Robert decides that honesty is the best policy when it comes to his relationship with Amy, so he tells her about his recent reunion with ex-wife Joanne, which does not go over well with Amy. To make matters worse, when Amy runs to Debra for consolation, Debra mistakenly spills the beans about Robert's recent fling with Stefánia.
Ray inadvertently commits petslaughter on Ally's hamster while Debra and the kids are away for the weekend. When Ray breaks the difficult news to Ally about Pumpernickel's untimely demise, Debra insists that they give the beloved pet a proper burial, complete with eulogies, but Ray thinks that it's ridicules to morn a pet.
The competition for attention between Ray and Robert reaches an all-time high with the brothers ending up in a fight. Ray's dreams of authoring a sports book get squashed when the publishing company takes a pass on it. To make matters worse, Robert receives the good news that he is being promoted to lieutenant.
Ray is mortified when he meets a girl whom he dated 25 years earlier and believes he treated with disrespect. Meeting Elizabeth again, Ray, wracked with guilt because he feels he didn't behave properly on their high school date, is determined to apologize. However, when he finds out the real reason Elizabeth went out with him that night long ago, he regrets ever bringing up the past.
Ray gets to go to the Super Bowl and cover it for his newspaper. He brings Gianni but feels bad about not having brought Debra when he sees that all the other reporters brought their wives so he has her flown in and to prove that he wants to spend time with her he rips up the tickets to the Super Bowl.
Robert gets a surprise visit from Stefánia, the woman with whom he fell head over heels in love when the Barones went on holiday in Italy. Robert's excitement over having his summer love Stefania so close quickly gives way to annoyance when he is witness to a few of her idiosyncrasies. Meanwhile, Stefania's father, who has accompanied her to America, has his own change of heart with respect to his feelings for Robert.
Ray purchases a new state-of-the-art vacuum cleaner from an attractive door to door saleswoman and it ignites a housekeeping war between Marie and Debra. Determined to prove to Marie that she's is just as good at "keeping house," Debra attempts to use the new vacuum to find some dirt, any dirt, in Marie's home.
Marie gathers Robert's ex-girlfriends Amy and Stefánia and his police partner Judy, so they can dissect his character in an effort to help her better understand why her eldest son can't commit to a relationship. Unfortunately, Robert unexpectedly drops in and is forced by his mother to listen to his character being assassinated by the women as they discuss his relationship hang-ups.
Thinking it would be hilarious to show the party-goers a typical day in the life of Frank and Marie, Ray and Debra do a dead-on impersonation of the two that brings down the house at the party. But when Frank and Marie turn the tables and do a Ray and Debra imitation, the couple finds it much less funny.
Depressed that Marie and Debra can't resolve their differences, Robert decides to join a support group and his cousin Gerard convinces him to attend a Inner Path meeting. The Romano family is concerned that Robert has joined a cult, and Marie insists that Raymond join Robert doing an upcoming meeting, so that he can keep an eye on his brother.
After arguing with Ray over his inability to help her with the household tasks, Debra becomes intrigued when their friends, Linda and Bernie, mention they've been seeing a marriage counsellor. Although Ray is against the idea, he quickly adopts a cooperative attitude when they meet the therapist, Pamela.
Robert think he has finally found "the one," and her name is Angela, an international-trade lawyer. She's bright, speaks four languages, and clearly likes Robert. The girl goes on to endear herself to Debra by complimenting her lemon chicken. Ray is also smitten with Angela, until he sees something disturbing during dinner.
While Raymond, Robert, and Frank don't want to bring up the fact that Marie is having vision trouble, Debra decides to level with her and suggests she visit an eye doctor. When Marie gets a pair of glasses just in time for the holidays, she winds up spotting and pointing out everyone's physical insecurities.
Boisterous Frank learns a difficult lesson in humility from his granddaughter, Ally. During a trip to the supermarket with Ray and Ally, Frank starts nibbling on some trail mix and is caught by a testy manager, and a heated argument ensues. Watching it all unfold is Ally, who becomes frightened by Frank's ranting.
Yet another bump appears on the rocky road to Robert and Amy's wedding, when the bride-to-be puts her betrothed in charge of writing the wedding invitations. Ray and Frank can't believe Robert let himself get roped into planning the wedding, they nevertheless come up with a plan to help ensure that Robert will never have to help out with the wedding again.
Ray takes Ally over to her friend Molly's house for a sleepover. He is mortified when Molly's mother turns out to be Peggy, the same Frontier Girl troop scout leader that he had a run-in with doing the cookie sale last year. Things get awkward when she pats his rear after he helps her set up a tent for the girls.
Debra throws the bridal shower for Amy, but her good intentions get sidetracked by Marie's overzealous participation. This leads to a fight between the two and Marie winds up leaving. Debra then gets a little to much to drink and ends up falling a sleet in her car with the key still in the ignition. She is awoken by a police officer who arrests her for being drunk behind the wheel.
When the MacDougals are invited to spend Easter with the Barones, the two families attempt to bond over a 500-piece puzzle. While everyone else gets frustrated with the puzzle, Ray and Pat continue working on it until the wee hours of the night while sharing stories about themselves and their families.
Robert has been discovered. While he and Amy are out buying Chinese food, a modelling agent gives Robert his card. Robert and Amy tells everyone about the modelling opportunity and Robert later goes to the agency for his first profile shoot. Ray, who really wants to meet the models, especially the Swedish kind, accompanies Robert to the agency, but when they get there, everything has mysteriously disappeared.
When Debra and Marie have a big fight, Ray is worried that Debra's anger will cause her to forget about their sex date that night. But rather than forgetting, the opposite happens when that anger is making the sex even better. Ray really enjoys the angry sex, so he starts doing things which makes Debra angry on purpose.
Debra wants Ray to clean up after himself and not leave things around the house, Ray wants Debra to stop moving his things. So when Robert stop by with a gift for Raymond, a letter from his idol, Mohammed Ali, Ray makes a point of putting the letter in the kitchen drawer. Unfortunately, when Debra later goes looking for a coupon in that same drawer, she finds it a mess and decides to dump its content in the trash.
Robert discovers Pat smoking and she pleads for him not to tell anyone. When Amy later smells smoke on Robert, she tells everyone that he has been smoking. When Pat doesn't tell the truth, Robert ends up being yelled at. The next day, he tells Ray and Debra the truth, but it doesn't take long for the two to blurt out the secret in front of everyone, which leads to many more secrets being revealed.