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.

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.

Ray finally tells Frank and Marie how he feels about their constant intrusiveness after Marie accidentally drives the car through the front of his house.

Robert finds himself in the most unlikely position of having to choose one of three women – girlfriend Amy, ex-wife Joanne or Italian bombshell Stefania – to share the future with him. Robert decides that ""honesty is the best policy"" when it comes to his relationship with Amy, so he foolishly tells her about his recent reunion with ex-wife Joanne. To make matters worse, when Amy runs to Debra for consolation, Debra mistakenly spills the beans about Robert's recent tryst with Stefania. Suddenly, Robert is not in a position to decide which woman he wants. It's a matter of which one, if any, is going to want him.

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 -- to help the youngster get through the grieving process. What Ray at first thought was an utterly ridiculous way to mourn the passing of a family pet, ends up being one of the most emotional experiences of his life.

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, just as Robert receives the good news that he is being promoted to lieutenant. The Barone family doesn't quite know how to react to this most bizarre of situations in which Ray has failed at something while Robert has succeeded. But worst of all, Ray doesn't know how (or if) he's ever going to get past this.

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. Meanwhile, Debra demands that Ray give her an example of something he regrets, but incredibly he can't come up with anything.

Robert starts to date a 22-year old woman and Marie and Debra don't think it's right. They break up when he finds out that she's really only 19 and she finds out that he's really 43.

While celebrating Thanksgiving, Debra discovers that her seemingly contented parents are really not very happy with each other. When Ray accidentally overhears his in-laws going at it with each other, he relays the news to Debra... who has always believed her parents' relationship to be a lot healthier than Frank and Marie's. But, when things come to a head at the Thanksgiving table, it's apparent that there really isn't that much of a difference between the two older couples – much to Debra's dismay.

Ray gets sneezed on at the airport and he fears he might have caught something so Debra tries to take care of him but Marie takes over.

Ray buys Debra an elaborate Christmas gift in the hopes that she will be so impressed, she will let him go on a weekend golf trip with his buddies. Ray believes he has the whole scenario worked out. He thinks by giving Debra a better gift than she is getting him will soon have him teeing off on a new course that he's been dying to play. However, he doesn't figure on the even more extravagant gift that Debra has purchased for him.

When Ray doesn't react to Debra's choking everyone makes fun of him so he tries to be more attentive in relative situations.

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.

Ray is mortified when he realizes that Marie used to read the personal journal he kept as a teenager. When Marie blurts out an embarrassing incident from Ray's past, he can't figure out how she could have possibly known that information. That is, until he discovers that she must have broken the secret code he used when writing in his journal. And in the process, his mother has learned about his most personal, and perverted, thoughts.

Ray and Debra discover that they have nothing to talk about except the kids.

Ray is upset when he finds out that Debra signed up Michael and Geoffery to play fairies in a school play.

Robert gets a surprise visit from Stefania, the woman with whom he fell head over heels in love when the Barones vacationed in Italy. Robert's excitement over having his beloved, and stunningly gorgeous, Stefania so close quickly gives way to annoyance when he is witness to a few of her idiosyncrasies. After spending some quality time with the Italian beauty, sans gelato and gondolas, Robert has to rethink his feelings for her. 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. Debra is as taken with the new vacuum as Ray once she witnesses all of the wonderful things it can do. That is, until she learns why the saleswoman showed up at their door in the first place. 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. Of course, the results are disastrous

Tempers flare when Marie accuses Debra of not returning a borrowed canister that holds sentimental value and Debra insists that she has already given it back. Debra is then horrified when she discovers that she does indeed still have the canister in her possession. With Ray and Robert's reluctant assistance, she concocts an elaborate scheme to get rid of the evidence, rather than confess to Marie that she was wrong and her mother-in-law was right all along.

Debra becomes angry when Ray contributes $1,000, without first consulting her, to his friends' harebrained scheme to open a go-cart business.

Marie gathers Robert's ex-girlfriends Amy and Stefania and his female police partner, Judy, together 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 in detail and compare notes on his quirky dating behavior, inability to commit to one woman and his flawed personality.

When Ray realizes that his kids would rather spend time with their Uncle Robert than with him, he decides to do something about the situation. When Robert makes the observation that, as a parent, Ray finds it boring to be around his kids, Debra couldn't agree more. She then suggests that Ray follow Robert's example and to try to have more fun with his children. But, when her own parenting skills are called into question by Marie, Debra quickly changes her tune and rallies behind Ray, insisting that they are both very involved parents.

When Ray and Debra find Frank painting their house, they find out that Marie put him up to the job due to his retirement. But, when Frank paints it the color they don't like, Ray fires him. That's when Marie reveals the truth behind Frank's retirement.

As Ray escorts Ally to a father-daughter dance, he realizes how grown up and independent his daughter has become. As a result, he begins to recall the day, nine years ago, when the Barone clan welcomed her into the family, but not without incident. In the flashback, expectant parents Ray and Debra are caught by surprise when Debra goes into labor in the back seat of Robert's patrol car, forcing him to be called into action. Meanwhile, Ray and Debra plot to keep a pushy Marie away from the delivery room until after the baby is born, not an easy feat.