Ray is devastated when he discovers his family lied to him about his television debut on a sports talk show. When he gets a second chance to appear on the same show, his family decides it's time they gave him some pointers on how to correct his awkwardness with certain words.
Ray suffers an anxiety attack while playing golf, after he tricked Debra into letting him go. Believing that he is sick, Ray goes to see a doctor who tells him that he is properly suffering from stress and that he needs to find a way to relax, such as playing more golf.
At a big surprise party for Frank and Marie's 40th. wedding anniversary, Ray is shocked to learn that his parents were once separated for a year and that they might have gotten divorced, if Frank hadn't returned because Ray broke his arm.
Ray, feeling guilty about only getting his dad a card for his 65th. birthday, makes up for it by buying him a fancy and expensive aquarium just like the one he always admired in the Chinese restaurant. Frank, at first adores the gift, but after one of the fish dies, he starts hating it.
Ray makes a startling discovery when he takes Debra to his 20th. high school reunion. It turns out that Debra's "one of them," them being the cool people who hated him and used to push him into the girls' bathroom.
When Marie crashes and ruins her Tupperware party, Debra decides that she's had just about enough of her mother-in-law's constant interference. She puts pen to paper and writes a letter to her mother-in-law.
Feeling left out when he thinks that his father selectively asked his brother to join a Civil War re-enactment, Ray voluntarily enlists for the Battle of Gettysburg. As the men prepare for Battle, a funny thing happens, Ray is finally able to tell Frank that he wishes they did more together.
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.
When Raymond chooses his mother's spaghetti and meatballs over his wife's lemon chicken for dinner, Debra blows a gasket. With good intentions, Ray asks his mom to teach Debra how to make her world-famous dish.
When Raymond takes over the family chequebook to prove to Debra how "easy it can be," he discovers he is no accountant after quickly running out of money and cheques start to bounce.
Raymond decides to accompany his brother Robert, who is a policeman, on a ride-along. Initially, spending night shift in the back of Robert's patrol car bores Raymond, but his boredom quickly turns to terror during a chance visit to Nemo's restaurant.
The scary monsters in her room send Ally scurrying nightly to the safety of her parents' bed, so sleep-deprived Ray decides it's time to call in an expert.
Debra brings pretzels to Ally's T-ball game, and when the person in charge of snacks tells her that pretzels aren't on the approved list, Ray doesn't stand up for her, prominently displaying his fear of being disliked by anyone.
Robert proves to be a crashing bore when it comes to teaching traffic school, so he decides to practice his presentation on the Barone family, which drives them crazy. In an attempt to lighten things up, he puts in an assist-officer call to Traffic Cop Timmy, a puppet dressed as a policeman.
When six-foot-tall Raymond discovers that he's shrunk a quarter of an inch, the resultant midlife crisis grows until it turns into an end-of-life crisis. So, before he gets put six feet under, he decides to make a list of his dreams and goals in life.
As the entire family prepares for Honest Frank's Yard of Bargains, Ray is surprised to see Debra unloading their cribs and baby clothing for the sale, and even more surprised to hear that she assumed they were done having children.
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.
While the Barones prepare for a friend's wedding, Ray kiddingly asks Debra, "Why did you marry me?" When she hesitates, he flashes back to the not-so-magical night 10 years prior, when he popped the big question.
