When Ray's house is tented for termites, he and his family moves into his parent's house and gives Frank and Marie a taste of their own medicine. Marie's initial excitement that "Raymond has come home!" quickly fades, when the world's greatest home intruders start to feel intruded upon.
After Frank has one car accident too many, Debra decides that the kids can't ride with him anymore, which makes Ray realizes that his dad is getting older.
Feeling overwhelmed with her responsibilities, Debra decides to get a babysitter. But when Lisa, the babysitter, becomes the smash hit at "Space Station Barone" with her alien-catching games and endless energy, Debra starts to get jealous.
After Raymond begrudgingly agrees to be the auctioneer at the Our Lady of Faith School auction, he's pleasantly surprised with the laughs he gets at Debra's expense. Debra tells him that she's going to get even, but later retracts her warning, but it's too late, Ray is convinced that Debra is plotting her revenge.
When Debra's mother comes to visit the family for a week, she is disappointed that her mother doesn't want to help around the house or that she doesn't show any interest in her grandchildren. Debra finds herself shocked to discover that she wishes her mom was more like Marie.
After Debra suggests that she might be more consistently romantic if she weren't in charge of the birth control, Ray decides to "cut the wires." But after a discussion with Robert and other guys, chickens out. But he does muster enough courage to go to the drugstore and buy "the stuff."
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.
It has been Ray's life long dream to get an article published in Sports Illustrated. So when his friend and coworker Andy, the "stats guy" at work and novice sportswriter, sells a piece to the magazine, Ray is devastated.
Raymond is in a bad mood. Forced to wait home all day for the delivery of Debra's new curtains, he can't go play golf and laments to his brother, that marriage is like a prison. So, when Amy breaks up with Robert, everyone blames Raymond.
Since Debra's parents will be out of the country on Thanksgiving Day, she, Ray, and the kids make plans to spend the holiday at Frank and Marie's house. But their dreams of turkey with sausage stuffing and yams with marshmallows on top are quickly shattered by Marie's new heart-healthy diet.
Robert has moved into a new apartment, and Raymond is jealous. Not because of the apartment, but because everywhere he looks, beautiful women are coming out of the woodwork, and they all seem to come by Robert's apartment.
Ray is overjoyed by the reaction he is getting from friends and family who received a personalized "Barone" toaster from him for Christmas, even Debra's parents seemed thrilled with it, but not having heard from them, Ray decides to visit his parents to find out what they truly think about present.
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 Marie discovers that Ray held an unchaperoned party at their home some 20 years ago, she is hurt and disappointed that her favourite son lied to her. Unable to forgive or forget, Marie can no longer put Ray on a pedestal, and he's been bumped for big brother Robert, and it's killing the needy Raymond.
Robert's entire demeanour changes when he starts clubbing with his patrol partner, Judy, and her friends. When he starts using expressions such as "this is so whack" and "I'm down with it," and showing up in mustard coloured suits, the Barone family find it hard to believe how much Robert is changing in order to fit in with his new friends.
Frank is elected Man of the Year down at the Lodge, and Marie enlists the reluctant Ray and Robert to prepare his tribute.
Just as Frank and Marie are about to embark on a Caribbean cruise, Frank hurts his knee and can't go. Ray, not wanting to disappoint his mother, accompanies her on the cruise. Marie is having the time of her life soaking every ounce of fun in the sun, while back home, Robert is just about out of patience being the caretaker for the injured Frank.
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.
Trying to impress Robert when they visit the Baseball Hall of Fame in Cooperstown, Ray uses his "weight" as a sports writer for Newsday to jump to the front of the line to meet the members of the ’69 Miracle New York Mets.
When Ray confides to Debra that her constant need to cuddle and "be on top of him" when they are sleeping is causing him many sleepless nights, Debra is more than happy to comply with his request to give him his space in bed.
Debra and Ray feel tremendous pressure to show each other a good time on a romantic weekend getaway in Vermont. From the moment they set foot in the quaint bed and breakfast, it's apparent that Debra and Ray are trying a bit too hard for this to be a perfect weekend.
When Debra gets a part-time job at an AD agency, an unhappy Ray is left to fend for himself and Marie is left wondering what's to become of the children, the house, and her beloved son now that they will be neglected.
When Ray and Debra realize they're nicer to strangers than to each other, they vow to change their ways.
After Ray urges Debra to go swing dancing with Robert, he can't believe how infatuated the two become with their new hobby, and it's starting to tick him off. Meanwhile, Ray sees a side of Marie that he never expected.
When Robert and Amy have sex in Robert's apartment, they forgot to close the curtains. It doesn't take long for the other tenants to launch a partition to make curtains mandatory. Humiliated, the loving couple are desperate to find a new make-out spot. Debra wants Ray to help them, so he offers Robert and Amy the Barone household basement.
Memories of how they first met flood back when Ray and Debra prepare Ally for her first play date with a boy.
