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.

Ray is devastated when he discovers his family lied to him about his television debut on a sports chat show. When he gets a second chance to appear on the show, his family decides it's time they gave him some pointers on how to correct his awkwardness with certain words. While Ray tries his best to remember his family's advice, his guest appearance turns out to be even more disastrous than the debut.

Ray's love of the links is in jeopardy after he tricks Debra into letting him play golf, and his guilty conscience translated into a big bogey. Marie gives Debra marital advice, much to Debra's dismay.

When six-foot-tall Raymond discovers that he's shrunk a quarter of an inch, the resultant midlife crisis grows until it stretches 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. But when Debra finds him writing his "Things To Do Before I Die" list, she decides to show her husband the proper way to have his crisis. Meanwhile, Marie gets mad at Frank when she discovers that he sold half of their burial plot for a profit.

After Raymond asks Debra why she ever married him, they take a walk back in time to the very beginning of it all. Raymond is very, very nervous. He's about to propose to his lovely girlfriend Debra and nothing is going right. But when he finally pops the big question, she accepts, the families celebrate, and all is well. At least for five minutes. Then the "nervous" turns into "pure fear" when Ray wonders if she really wants to marry him for love or if it's just for the elaborate wedding she's been planning since she was twelve.

While the Barones prepare for a friend's wedding, Ray kiddingly asks Debra, "Why did you marry me?" When she hesitates, he flashes back to the not-so-magical night 10 years before when he popped the big question. Ray gets unexpected, unsolicited and unwelcome help with from his parents, but Debra says yes anyway. That leaves the gloomy groom wondering if she did so because she loves him or because she felt pressured. So, Ray decides he's "gotta give her another chance to say no."

Raymond is in a bad mood. Forced to wait home all day for the delivery guy to bring Debra’s new curtains, he can’t go out and play golf and laments to his brother that marriage is like a prison. So, when Amy breaks up with Robert after he says he cannot commit right now, everyone blames Raymond for ruining his brother’s life.

When Debra and the kids go away for the weekend, Ray is forced to confront the real reason he doesn’t want to stay home alone. What should have been a couple of days of bachelor living and freedom from responsibility for Ray instead turns into a harrowing experience — that can be traced all the way back to his childhood. Rather than enjoying the rare peace and solitude at his own home, Ray actually chooses to head across the street and spend time with Marie.