In this flashback episode, Ray and Debra remember their days in their first apartment. Debra finds out she's having twins, and so they decide they need a house. Ray maps a strategy where they are not close enough for everyday visits from his folks but not far enough for overnight stays. A mustached Robert discovers his wife wants a divorce. Part-time realtor Frank finds Ray and Debra a perfect house across the street from him and Marie. Debra decides living across from her in-laws is a good idea.
Ray brings home a stray bulldog that reminds him of the dog he had to give up as a boy due to his allergies, but his brother, Robert, bonds with the animal and the siblings then have to decide who gets to keep him. When the owner of the dog arrives at the Barones' to pick up what turns out to be her prize-winning stud, she discovers that he has been fixed and isn't worth anything to her but that he means everything to Ray and Robert.
When Debra tries to change Ray's pessimistic attitude about winning the "Sports Writer of the Year Award," he agrees to change his ways and become more upbeat – and suffers the downside of being the only optimist in his family. When Ray finally starts feeling good about himself and his recent accomplishments, his family is surprised by the change in his personality and accuses him of being a "bragger with a swelled head."
When Ray and his family play a game of "Scruples" after their cable goes out and they have nothing but time on their hands, they find themselves arguing about honesty. To make matters worse, when Ray complains to the cable company about the disruption in service, he is informed that he has an illegal hookup – courtesy of his dad.
Debra, already annoyed at getting stuck driving the old car Ray bought from his parents, really gets upset when she discovers that it was his old "make-out-mobile." Debra had been unable to understand why Ray wanted so desperately to buy his parents' old car, until Robert mistakenly blurts out that it's the car in which Ray first "got lucky" as a teenager with his girlfriend. Imagining what might have happened in the car during its earlier life, Debra decides not to drive it again.
Raymond can't face the fact that everybody thinks that his brother Robert is "classically handsome," while he is merely "adorable like a hamster." Robert is reluctant to go on a date because he's insecure about his appearance, so when Debra tells him he's attractive, Ray starts feeling insecure about his own looks. Ray's jealous of his brother's looks when he overhears Debra compliment Robert. So, Ray decides to get a head-to-toe makeover to impress Debra, including a fake tan like George Hamilton.
Ray discovers, after many years, that the autographed Mickey Mantle ball he got as a kid from his father isn't authentic. Feeling hurt by the fact that his father was not truthful about the ball, Ray decides he's going to tell Ally the truth about Santa Claus. But when two familiar looking Santas unexpectedly show up at his house to surprise Ally, she's even more confused – about the truth.
When Ray's "free" time goes to coaching his 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. When Robert is forced out as captain of Nemo's basketball team, Ray gets the title and the opportunity to lead his team to victory. Meanwhile, Frank and Marie are upset with Ray for de-throning Robert as captain, and feeling guilty Ray begs Robert to re-join the team.
Although Marie has always cooked the traditional turkey dinner for Thanksgiving, Debra decides it's her turn to prepare the holiday meal, but, not wanting to compete with Marie's turkey, she chooses to serve fish which upsets the apple cart. Marie, feeling threatened when her family thinks Debra's fish idea is perfectly acceptable, decides to bring her own turkey to the dinner party to prove that she's the better cook. Meanwhile, Ray's idea of a traditional holiday at home becomes even more untraditional when the relatives opt not to watch football.
Ray gets tired of being treated like a kid at his father's poker game, so he ignores his father's advice and ends up losing all his money. Debra wants Ray to act like a mature adult and ask Frank for his money back, but Ray is too stubborn. Meanwhile, it turns out that Frank was only trying to teach Ray a lesson - that you can always go to your father and he'll make everything okay.
When Ray's upper class in-laws come for a visit, he begs his parents to be nice to them and accept their differences even though their lifestyles are worlds apart. Ray admits to his parents that he doesn't always see eye-to-eye with Debra's folks but manages to fake it and he'd like his parents to do the same when they all go out and try to have a family dinner. The request, however, proves to be a tall order for Frank and Marie.
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. Frank, feeling he has a new lease on life, convinces Ray to submit his story ideas for the column, which he plans to call "I Was Just Thinking." Ray then has to break the news to his father that the editor thinks Frank's writing is the most embarrassing work he's ever read.
Nemo's niece, Angelina, takes employment at Nemo's as a waitress at Nemo's. When Angelina catches Ray's eye, he has a lot of explaining to do to his wife, Debra especially when Angelina calls him at home. Ray accidentally leaves his wallet at Nemo's, and Angelina calls him at home to let him know she found it. But, because he feels guilty about his innocent attraction, Ray denies ever knowing her. When the situation is blown out of proportion by the Barone family, Debra decides to visit Nemo's to see what all the fuss is about.