Season 5

When Marie surprises the family with the news that she's treating them all to a two-week vacation to Italy, everybody loves the idea except Raymond. 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, the sights, and tastes of the country.

Ray is complaining about the heat, Debra is getting tired of following Marie's strict schedule and of Ray's pessimistic attitude, Robert meets Stefánia's father, who is not thrilled with his daughter choice of man, and Frank is enjoying himself playing pétanque. After going on a long walk with his mother, Ray slowly starts to enjoy himself and appreciate where he is, no thanks to Marie.

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 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.

Robert starts to date a 22 year old woman and Marie and Debra don't think it's right. Things take a turn when he finds out that she's really 19 and she finds out that he's really 43.

While celebrating Thanksgiving, Ray discovers that Debra's seemingly contented parents are really not happy with each other. When things come to a head at the Thanksgiving table, it's apparent that there really isn't that much of a difference between Ray's parents and Debra's parents.

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. 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.

When Marie blurts out an embarrassing incident from Ray's past, he can't figure out how she came by that information. He is mortified when he realizes that she used to read the personal diary he kept as a teenager.

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 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.

Tempers flare when Marie accuses Debra of not returning a borrowed canister that holds sentimental value. Debra insists that she has already returned the canister, so she is horrified when she discovers that she still has the canister in her possession.

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

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.

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 Ray finds it boring to be around his kids, Debra couldn't agree more and suggests that Ray follow Robert's example.

Debra gets upset when she finds out that her parents have separated.

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 colour 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.