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.

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.

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.

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.

Frank is so green with envy that he forces Marco to choose either Marie or him as a friend. Meanwhile, Ray sides with Frank because he doesn't approve of a married woman (especially his mother) having a male friend.