Nemo's niece, Angelina, takes employment at Nemo's restaurant as a waitress. When Angelina catches Ray's eye, he has a lot of explaining to do to his wife, especially after Angelina calls him at home.

When Frank gets a few anecdotes published in Reader's Digest, he submits his writing samples to Ray's editor, hoping to get his own column in the newspaper.

When Ray's free time goes to coaching Nemo's basketball team in preparation for the Pizza League championships, he is reminded by Debra that their kids are growing up fast and he's missing precious time with them.

Ray finds out that the diamond on Debra's engagement ring is a fake, so he steals it from her to get it changed, only to find out after that she already had it exchanged it with her grandma's $15,000 diamond.

A popular radio psychologist visits the Barone household to interview Debra for a book on the American family. But the doctor finds that the rest of the eccentric Barones are more captivating.

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.

Debra discovers that her mother-in-law, Marie, likes Robert's girlfriend, Amy, better than than her, because Amy is a "good girl."

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.

Feeling pathetic because he lives with his parents, Robert finally musters up the courage to move out on his own. Encouraged by Ray, and much to his parents’ horror, Robert packs up his bags, takes his dog and moves into a garage apartment.

When Ray finds out that his father let him win a game of ping pong when he was twelve, he challenges him to a new game.

When Debra and the kids go away for the weekend, Ray is looking forward to a couple of days of bachelor living. But instead of enjoying himself, the night is turns into a harrowing experience, and Ray is forced to confront the real reason he doesn’t want to stay home alone.

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.

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.

While out for a family dinner, the Barones spot Robert's ex-wife Joanne, which prompts them to reminisce about the demise of his marriage. The family tells Amy the truth about Robert's failed marriage. The surprise sighting also brings back some personally harrowing memories for Robert.

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 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.

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.

It's the first Thanksgiving since Debra's parents divorced, and Debra is thrilled that both her parents have agreed to have dinner with the Barone family. However, she soon learns that her father is bringing a date. Everyone is horrified except Debra's mother, who thinks it's just great.

When Marie receives a Christmas letter from a relative detailing how wonderful her life is and how well her kids are doing, it drives Marie insane with jealousy. Later, when Marie shows Debra the letter, the two join forces to compose a Barone family Christmas letter.

Robert is ecstatic when he is up for a job at the FBI. That is, until he learns that Marie's intrusive ways may be his undoing.

Ray has been arming himself with knowledge and has been preparing to speak with Ally about the facts of life only to find that Ally's interest has changed from where babies come from to the meaning of life.

The feud between Debra and Marie continues. Ray realizes that he can use the feud to get Debra to do almost anything for him, dragging Frank into exploiting the situation with Marie.

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.

Robert gives Ray a great idea on what to get Debra for Christmas, but he isn't very happy when Ray takes all the credit for it.

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 and Debra wind up in a two-week stand-off over a suitcase.

Ray and Debra get caught up in telling lies in order to cover up previous lies. When the lies snowball out of control, Marie picks up the scent and traces everything back to the initial lie.

Robert and Amy convince their families to spend Thanksgiving together. When the Barones arrive at the Pennsylvania home of Amy's parents, they find that their differing family traditions encourage lots of lively conversation.

Robert reveals that he has taken a second job selling home security systems, and that he has been asked to join the security firm full-time. But of course, this would mean retiring from the police force early.

Robert and Ray end up with the mother of all guilt trips when they decide not to help their mother with a home project. The reason they skip out is so that they can land a prime spot on the golf course, by waiting in line in their car all night.

Upon returning from visiting friends at a retirement community in New Jersey, Frank and Marie tell the family that they plan on moving there. Not unsurprisingly, everyone is overjoyed hearing the news.

After Amy spends an hour chatting with Ray while he is trying to watch the basketball game, he tells Robert that she talks to much, which of course, Robert repeats to Amy, leading to a confrontation between Ray and "Lady Chatterly."

Ray's latest manipulative plan involves constantly turning down Debra in the bedroom.

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.

Ray fears getting his adenoids removed, but Debra convinces him to go through with the surgery. At the hospital, while Marie is in the bathroom, and everyone else in the waiting room, the nurse comes out and tells Debra that Ray isn't waking up from the anaesthesia.