When Ally wants to quit learning the piano, Ray decides to resume his interest in the piano in order to teach his daughter a lesson about quitting.

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.

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.

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.

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.

Ray is bewildered, but not altogether displeased when Debra starts initiating sex on a more than regular basis. He can't believe his luck, he is even willing to give up his golf game to satiate Debra's newfound desires. But he can't leave well enough alone, and decides to look into the reason behind his wife's sudden burst of energy.

While celebrating Thanksgiving, Ray discovers that Debra's seemingly contented parents are really not happy with each other. When things come to a head at the Thanksgiving table, it's apparent that there really isn't that much of a difference between Ray's parents and Debra's parents.

When Debra stumbles across a cassette tape that contains a message from Ray's college girlfriend, she wants to know why he has saved it all of these years.

After deciding to lend Robert $1,000 when he complains he's struggling with finances, Ray and Debra are surprised when Robert uses the money for a vacation to Las Vegas.

Ray throws a lame bachelor party for Robert and is shamed by Debra, Marie, and Amy into throwing him a proper one at the lodge, which will also be attended by Amy's father and brother.

When the kids ruin Ray's dictionary, Frank shares the story of how Ray ruined his priced jazz collection. After trying to make amends for his childhood mistake, Ray discovers that he may not have been the culprit.

Amy's parents put Robert on the defensive when they point out his compulsive habit of touching food to his chin before he eats it.

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.

Ray is elected to tell Debra that members of the P.T.A. have problems with the way she dresses.

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.