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 finds out that the diamond on Debra's engagement ring is a fake, so he steals it from her to get it changed, only to find out after that she already had it changed. She had her grandma's $15,000 diamond put in.

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.

Debra discovers that her mother-in-law, Marie, likes Robert's 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 Debra's 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.

Feeling pathetic because he lives with his parents, Robert finally musters up the courage to move out on his own. Encouraged by Ray, and much to his parents’ horror, Robert packs up his bags, takes his dog and moves into a garage apartment. But the move affects the family more than they anticipated. They feel the absence of their relationship “buffer.” As Debra describes it, “He’s like.the lead apron at the dentist.” Meanwhile, Robert enjoys his newfound freedom, until Raymond comes to visit and points out that the older couple with whom he is living are really carbon copies of their own parents — from whom he was trying to get away.

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.

Debra and Ray feel tremendous pressure to show each other a good time on a romantic weekend getaway in Vermont. From the moment they set foot in the quaint bed and breakfast, it’s apparent that Debra and Ray are trying a bit too hard for this to be a perfect weekend. Debra agrees to a tour of the Ben and Jerry ice cream factory while Ray suggests they check out a local antique fair. Meanwhile, Marie spies on Robert, who is left to babysit for the kids.

When Robert and Amy get caught alone by some of Robert’s fellow apartment tenants, they are desperate to find someplace, any place, where they can have some time to themselves. Ray comes to the rescue, at Debra’s urging, by allowing Robert to move into their basement for a while. But, when caught again, by someone even more intimidating – – the couple is mortified.

Inspired by how well the Barones got along at Thanksgiving dinner, Debra is intent on finding a way to improve her relationship with Marie. When Debra spends the whole day cooking with Marie, it's the perfect opportunity to test out her new ""shrug it off and let the criticisms roll off your back"" attitude that she feels will win Marie over.or will it? Meanwhile, Ray gets roped into having Frank and Robert accompany him to a car show, where he has his own method of getting along with his family.

While discussing the possibility of having to hold Michael back for another year of pre-school, Ray is shocked to discover that he too was left back when he was that age. Once Ray learns of his scholastic past, he is convinced that of all the traits a parent could pass on to a child, his legacy is to pass his stupidity on to Michael. Meanwhile, Frank heads over to the school to sweet talk the kindergarten teacher into letting Michael advance with the other kids.

When Amy raises the notion that Robert's reluctance to commit to Amy may be a result of his being gay, Ray doesn't believe it. But, after further thought and closer observation of Robert's keen sense of style and panache for interior design, Ray is not so sure anymore.

Ray feels tremendous guilt when he cancels plans with Robert, who then gets hurt in the line of duty, when he should have been hanging out with his brother. At first, it's all laughs and snide remarks from Ray when he finds out the cause of Robert's job-related injury. Ray's bedside manner definitely leaves a lot to be desired. But, after some prodding from Debra, Ray decides to show Robert just how much he really cares for him...not an easy task for a Barone.

Ray and Debra renew their wedding vows after they find out that Ray accidentally taped over their wedding with the 1991 Super Bowl.

After losing his nerve on the job during his first day back from medical leave, Robert quits the police force. No one realized how much of an effect the ""bull incident"" had on Robert's mental state – and his ability to confront fear and the unexpected. Now, back on the job only one day, he finds himself too scared to handle a minor altercation so, rather than face his fears, he decides to change his career to something ""safer and more solitary"" – telemarketing. However, he rejoins the force after confronting the bull that gored him.

While out for a family dinner, the Barones spot Robert's ex-wife, which prompts them to reminisce about the demise of his marriage. The family tells Amy the truth about Robert's failed marriage to Joanne, whom Frank not-so-affectionately refers to as ""a nutcracker."" The surprise sighting also brings back some personally harrowing memories for Robert – although, when Joanne suggests the ex-spouses get together, Robert seems intrigued.

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.

Tempers flare when Marie accuses Debra of not returning a borrowed canister that holds sentimental value and Debra insists that she has already given it back. Debra is then horrified when she discovers that she does indeed still have the canister in her possession. With Ray and Robert's reluctant assistance, she concocts an elaborate scheme to get rid of the evidence, rather than confess to Marie that she was wrong and her mother-in-law was right all along.

Marie gathers Robert's ex-girlfriends Amy and Stefania and his female police partner, Judy, together so they can dissect his character in an effort to help her better understand why her eldest son can't commit to a relationship. Unfortunately, Robert unexpectedly drops in and is forced by his mother to listen to his character being assassinated by the women as they discuss his relationship hang-ups in detail and compare notes on his quirky dating behavior, inability to commit to one woman and his flawed personality.

Marie and Debra set up Amy with Gianni to get Robert jealous so he'll want to get back together with Amy but their plan backfires when Amy and Gianni hit it off.

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.

While Raymond, Robert and Frank don't want to bring up the fact that Marie is having vision trouble, Debra decides to level with her and suggests she visit an eye doctor. When Marie winds up with a pair of specs just in time for the holidays, she winds up putting the family on edge when she starts seeing them for better and for worse! Meanwhile, Robert gets back together with Amy and invites her to a Thanksgiving dinner.

Robert gives Ray a great idea on what to get Debra for Christmas, but he isn't very happy when Ray takes all the credit for it.

The six-year on-again, off-again relationship between Robert (Brad Garrett) and Amy (Monica Horan) is definitely on again in this pivotal episode. So much so, in fact, that ""Robert wants to propose to Amy,"" says executive producer Philip Rosenthal. But there's one formality the hopeful groom-to-be must take care of first: asking Amy's devout churchgoing folks (Fred Willard, Georgia Engel) for their daughter's hand in marriage. To that end, ""Robert convinces Ray to accompany him to meet her parents in [Pennsylvania],"" says Rosenthal. How they---and possibly Amy---respond determines whether wedding bells will be ringing anytime soon. Peter: Chris Elliott. Frank: Peter Boyle.

Amy's mom and dad finally meet the Barone Family. Amy's folks show up unexpectedly at their daughter's house on a Sunday morning. They want to talk Amy out of marrying Robert and take her home to Pennsylvania with them. First, they are stunned to see Robert there. Then Frank and Marie arrive. It doesn't take long for the two sets of parents to disliking each other.

Yet another bump appears on the rocky road to Robert and Amy's wedding, which was nearly blocked by her disapproving parents. When the bride-to-be (Monica Horan) puts her betrothed (Brad Garrett) in charge of writing the wedding invitation, he seeks input from Ray and Frank. While they can't believe Robert let himself get roped into such a chore, they nevertheless come up with a plan: If Robert makes a mess of the job, it will convince Amy that she should take care of all the wedding plans herself. So the groom drafts an appalling mock invite---complete with the wrong date and names---and waits for Amy's reply...which is worse than he ever expected.

Debra and Ray pick out replacement spouses for each other and jealousy starts. Marie announces that Rose, the elderly lady next door, has passed away. Marie is upset because Rose is the woman she'd chosen for Frank if she hadn't died. Debra thinks it would be fun to fantasize about who should take her place and tells Ray she's selected her friend Linda. But then Ray picks Linda's husband Bernie for Debra.

Debra gives a bridal shower for Amy, but her good intentions get sidetracked by Marie's overzealous participation. When Marie attempts to ""take over"" Amy's wedding shower, Debra gets upset and yells at her, prompting Marie to leave in a huff. Returning to the party festivities, Debra starts drinking a little too much champagne and winds up being too tipsy to drive. When she can't reach Ray on the phone, Debra decides to take a nap in her car with the keys in the ignition and is awakened by a police officer, who arrests her for drunk driving. When her license is suspended, Debra finds herself in a precarious situation when she's forced to rely on Marie for help.

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

Robert and Amy exchange vows in a classic Barone family wedding ceremony.