Episode: 028 | Aired:
At a big surprise party for Frank and Maries 40th wedding anniversary, Raymond is shocked to learn that his parents were once separated for a year and might have gotten divorced if Frank hadnt returned home to help with Rays broken arm. After the initial shock wears off, Ray starts to wonder if its his fault that his parents are together and miserable. If he had never fallen off his bicycle and broken his arm, Frank and Marie may have stayed apart, fallen in love with other people and had wonderful lives. But then Ray discovers that this time its definitely not his fault.
Episode: 046 | Aired:
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. Hes 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 its just for the elaborate wedding shes been planning since she was 12.
Episode: 047 | Aired:
Ray fears that Debra is more interested in the wedding than in him. With wedding plans in runaway train mode, Ray feels lost amid the endless discussion of veils, bands, appetizers and wedding vows. He is convinced that he is but a pawn in Debras dream wedding fantasy. When the big day finally arrives, though, Ray realizes he is marrying Debra, and she him, for all the right reasons.
Episode: 041 | Aired:
Debra discovers that her mother-in-law Marie likes Roberts girlfriend Amy better than she likes her because Amy is a good girl. When Robert accidentally lets it slip to Marie that Amy is a virgin, Marie is thrilled to pieces. Jealous of the attention Amy is receiving from Marie, Raymond minimizes Debras premarital activities, leading his mother to believe that Debra was a good girl too. When the family discovers why Marie has this sudden purity fixation, Robert and Raymond are in for a big surprise.
Episode: 025 | Aired:
At the urging of his parents, Ray takes his brother, Robert, out for a night on the town. But when Robert wants to get in touch with Rays feelings Ray gets a little uncomfortable with this brotherly bonding thing. Ray is left wondering if his goodwill gesture was really such a good idea after all.
Episode: 026 | Aired:
When Ally decides to stop taking piano lessons from her Grandma, Ray tries to teach her an important lesson about not quitting by resuming the lessons he took from his mother 25 years earlier.
Episode: 029 | Aired:
When Debra fears that Ray is hiding out at work because he doesnt want to spend time at home with the family, she asks him to start working from home - - but things dont turn out the way she planned. When Debra decides to be a nice wife and bring her hard working husband his dinner at the office, she is horrified to find him eating pizza and playing paper football with the guys and Pat OBrien. Upset, because she thinks he would rather be with them than with his own family, she gets Ray to reluctantly set up a home office complete with a fax, a modem, and a satellite dish. But once Raymond gets comfortable in his new surroundings, Debra cant wait to get him out of the house and back to the office.
Episode: 030 | Aired:
Sick of reading Ally the same stories night after night and in the mood to be a little creative, Debra decides to try her hand at writing a childrens book. Feeling great about doing something other than being a mom, she invites Raymond to write the story with her. But Debra sees the other side of her easy-going husband when he turns their little project into an all-out competition -- with Ally as the judge.
Episode: 032 | Aired:
At Debras insistence, Ray reluctantly takes her to his 20th high school reunion, and its even worse than he expected. It turns out that Debra is one of them -- the cool people who hated him and used to throw him into the girls bathroom. Depressed about being unmasked as a nerd, Ray tries to deal with the mixed marriage.
Episode: 034 | Aired:
All Ray wants for Christmas is a little loving from his wife and hes willing to try anything and everything to have his holiday wish come true. Ray has tried just about everything to get Debra in the mood and his dream comes true when she finally falls victim to his boyish charm on Christmas morning. The problem? At the very moment that he gives her the shivers, his entire family is working their way into the house for eggs Florentine and gift unwrapping. But where theres a will, theres a way -- and Raymond is determined to get what he wants from Santa this year.
Episode: 035 | Aired:
Feeling left out when he thinks that his father selectively asked his brother to join a Civil War re-enactment, Ray voluntarily enlists for the Battle of Gettysburg. As the men prepare for battle, a funny thing happens and Ray is finally able to tell Frank that he wishes they did more together. So, although Franks on the side of the North and Raymonds on the side of the South, the Barone soldiers are able to put their political differences aside and share much more than a Civil War handshake.
Episode: 036 | Aired:
When Rays Zia Sarina comes to visit all the way from Italy to help Ally with a school project on family trees, hes thrilled to finally meet a relative whom the whole family likes. She is instantly adored by her American family for her way with Pizza and Old World charm. Ray, as always, thinks its too good to be true -- and he turns out to be right.
Episode: 038 | Aired:
When Raymond takes over the family checkbook to prove to Debra how easy it can be to balance it, he discovers he is no accountant. After he quickly runs out of money and starts bouncing checks, he tries to hide the truth from Debra and winds up entangled in a mess of lies, two fake checkbooks and a large loan from his brother.
Episode: 039 | Aired:
When Raymond goes on a citizens ride along in his brothers patrol car and sees Robert risk his life during a hold-up, he gains a new respect for him. Spending a shift in the back of Roberts patrol car bores Ray at first and he wonders why he even bothered putting on a bulletproof vest. But his boredom quickly turns to terror during a chance visit to Nemos restaurant that puts him in the middle of a hold-up. When Robert saves the day by throwing a hot pizza in the burglars face, Raymond sees for the very first time how courageous his brother really is. Unfortunately, Raymonds attempt to put Robert in the spotlight backfires and he is forced to try his best to tell his older brother how he feels.
Episode: 040 | Aired:
When Ally, claiming that there are monsters in her room, insists on sleeping in her parents bed, Ray and Debra do everything they can to slay the monsters so they can get a good nights sleep. A sleep deprived Raymond wonders where the "How to Grow a Kid" book is when he needs it, especially when Ally still refuses to sleep in her own bed alone even after her Sicilian Slicer father slays the rooms monsters. Finally, Ray and Debra take turns sleeping with Ally in her bed. But when a tired and desperate Ray presses his mother into service without telling Debra, the whole house is up all night.
Episode: 042 | Aired:
Debra brings an unapproved snack to Allys T-ball game and Ray doesnt stand up for her, prominently displaying his fear of being disliked. Debra had no idea that pretzels were not on the approved snack list in the orientation packet for Allys team. And, as a mom juggling three children under the age of 7, she doesnt have time to cater -- and really doesnt care. But when Raymond wont take her side against the uptight team parents, she loses her cool and points out that hes just afraid of making enemies. But enemies he makes -- at the very next game.
Episode: 043 | Aired:
When Roberts traffic school students complain that his class causes severe insomnia, he practices on members of his family -- who turn out to be even tougher critics. Asserting that driving is a privilege, not a right, Robert uses teaching methods that leave his students cold -- and bored. So in order to spice up his classes, he practices on his not so willing family. After a few minutes, he loses their attention too -- until he creates a ventriloquist dummy named Timmy that is anything but dull, and appears to have a few issues with the Barone family.
Episode: 044 | Aired:
Debra tries to teach Raymond how to have a normal mid-life crisis, like everyone else, after he starts planning his burial. Triggered by the realization that hes shrinking and is no longer 6" tall, Raymond begins to go through a mid-life crisis. Sensing that he is troubled, his friends suggest that he really just needs some goals and dreams. 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 her half of their burial plot for a profit.
Episode: 045 | Aired:
When Debra gives away all the baby stuff at a family garage sale, Ray gets upset that she doesnt want to have any more children. Ray is surprised to hear that Debra just assumed they were finished having children. As usual, their private business becomes a family matter, and Marie reminds Debra that, You want to plant your seedlings before winter comes and everything freezes over. Eventually, their disagreement leads to a sentimental journey down the lane of messy memories past.