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.

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 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.

At a big surprise party for Frank and Marie's 40th wedding anniversary, Raymond is shocked to learn that his parents were once separated for a year and might have gotten divorced if Frank hadn't returned home to help with Ray's broken arm. After the initial shock wears off, Ray starts to wonder if it's his fault that his parents are still together... and miserable.

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 takes pen to paper and writes a letter to her mother-in-law, telling her to stop intruding into her life. Horrified by the problems that this letter might trigger, Ray does everything in his power to intercept the offending document – but he fails. Surprisingly, the family discovers that honesty really may be the best policy.

Robert proves to be a crashing bore when it comes to teaching traffic school, so he decides to practice his presentation on the 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.

Everywhere Ray looks, beautiful women are coming out of the woodwork to stop by and say “hi” to new tenant Robert. It’s the best looking “welcome wagon” Ray has ever seen. Unbeknownst to Debra, who believes him when he tells her that the brotherly visits are an attempt to cheer up a lonely, homesick Robert, Ray is having the time of his life pretending to live the carefree life of a bachelor – that is, until Debra shows up unexpectedly.

When Ray confides to Debra that her constant need to cuddle and “be on top of him” when they are sleeping is causing him too many sleepless nights, Debra is more than happy to comply with his request to give him his space in bed. Now, Ray is learning the hard way that you have to be careful what you wish for!

Debra is upset when her hippie, free spirit sister decides to become ... a sister. It's a good indication that something is up when Debra's sister, Jennifer, shows up for a visit with rosary beads and prayer cards as gifts for the kids. Unable to share the real reason why she is so upset with Jennifer's decision to become a nun, Debra reacts by accusing her sister of going through yet another phase and not being truly worthy of the calling to the religious life.

Debra throws the Barone family into turmoil when she finally creates a dish that everyone likes. Ray can't believe it when he samples Debra's braciole. Even though her past attempts at cooking seemed to have ruined his taste buds, it's simply delicious. But, when Marie gets wind of Debra's cooking prowess, and sees the effect that the braciole has on Ray, Robert and Frank, it's war!

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 starts to date a 22-year old woman and Marie and Debra don't think it's right. They break up when he finds out that she's really only 19 and she finds out that he's really 43.

Ray buys Debra an elaborate Christmas gift in the hopes that she will be so impressed, she will let him go on a weekend golf trip with his buddies. Ray believes he has the whole scenario worked out. He thinks by giving Debra a better gift than she is getting him will soon have him teeing off on a new course that he's been dying to play. However, he doesn't figure on the even more extravagant gift that Debra has purchased for him.

Held captive at Frank and Marie's during a snowstorm, Debra, Ray and Amy actually find themselves having a great time. Then Debra makes a nasty comment to Frank which totally upsets the good mood. This causes Marie to defend Frank and finally reveal her true feelings for Debra.