Everybody Loves Raymond: 10 Most Awkward Peter Moments, Ranked

Ray Barone and the rest of his dysfunctional family may be the stars of Everybody Loves Raymond, but the equally bizarre McDougall family have also been known to visit Long Island from time to time. Amy McDougall is Robert’s girlfriend and then wife, and her mild-mannered and religious parents often clash with the larger than life Barones when they come to town.

Amy’s brother Peter, played brilliantly by actor Chris Elliott, is one of the more colorful characters on Everybody Loves Raymond. This overgrown teenager boasts some unusual personality traits and interests which have contributed towards some of the show’s most awkward and cringe-worthy moments.

10 Trying To Ruin His Own Sister’s Wedding

When Robert and Amy finally tied the knot in a double-header of episodes in season seven. There was no chance that a Barone wedding would ever go off without a hitch, but the day was plagued by problems right from the start. Peter didn’t help matters by openly trying to sabotage the wedding when he “forgets” to collect the priest for the service, leaving the Minister to hitch-hike to the church. By the end of the day, however, Peter’s betrayal has paled in comparison with everything else that has gone on.

9 He And Robert Finally Bond Over Their Domineering Siblings

There are definite similarities between Robert and Peter and their relationships with their siblings, Ray and Amy, who they both perceive as being the “favorites” in the family. Peter may not think that Robert is good enough for his sister, and Robert may think that Peter is downright weird, but they do have one moment together when they find themselves bonding over being older brothers who are still living at home. It is one of the few moments when viewers feel sorry for Peter and his situation.

8 Getting Knocked Back At A Bar

In the season nine episode “A Date for Peter,” fans get to see the geeky side of comic book-loving, Peter. Debra takes it upon herself to try and set Peter up with a woman after he tells them a sob story about one time he was in a bar and finally plucked up the courage to talk to a woman he found attractive.

After he asked her how she was, the woman replied that she was “fine… but not desperate.” It gave viewers a glimpse into the dumpster fire that is Peter McDougall’s life.

7 Hanging Out With His Newly-Married Sister

Despite the fact that he tried his best to ruin her wedding day, Amy is still kind-hearted enough to forgive Peter and even allows her down-on-his-luck brother to crash on their couch for a while when he finds himself without a place to stay. Peter, of course, ends up taking advantage of that generous invitation and spends his time hanging around newlywed Amy and Robert’s apartment for a few weeks, and he simply will not take the many hints that Robert drops to show that he is not wanted.

6 Gossiping About Robert And Amy To His Parents

Robert Barone is an old-fashioned guy, and he decides in the season seven episode “Just a Formality” that he wants to do things right and ask Amy’s parents’ permission before they get engaged. Unfortunately for Robert, he doesn’t know that Peter McDougall hates him and that he has been gossiping to his parents about Amy and Robert behind their backs.

The religious McDougalls don’t like what they’ve been hearing from their son, some of which isn’t even true, and refuse to give Robert their blessing when he drives to their home to ask for Amy’s hand.

5 The Barone Family’s Attempts To Get Rid Of Him

It isn’t just Robert and Amy who try their hardest to get Peter out of their lives. The whole Barone family finds Peter a little weird—which is a bit like the pot calling the kettle black—and, in “Peter on the Couch,” they don’t do much to hide their feelings about having him around.

As Peter stands alone in Ray and Debra’s home, looking like a sad and unwanted puppy, we find the Barones whispering in the background about how they are going to get rid of him.

4 His One-Sided Friendship With Ray

This is especially hard for Peter to take because he has a bit of a man-crush on one of the members of the Barone family: Ray. For some reason, Peter takes a shine to Ray, and he becomes convinced somehow that they are best friends, even though Ray has never given him any encouragement in that department. It is pretty awkward to watch how Peter hangs on Ray’s every word, looking for a scrap of attention when all Ray wants to do is get as far from him as possible!

3 Ray Interrupting His Attempt To Chat Up Peggy

Ray and the rest of the Barones may find Peter weird and annoying, but Debra has always been willing to be more sympathetic to her brother-in-law. When she hears the sob stories about the disaster that it is his love life, Debra decides to throw a party and invite some of her female friends so that Peter can find a date. Peter and Peggy, Ray’s nemesis after their fight over cookies at a Girl Scout meeting, seem to be hitting it off, but Ray can’t stand that the two of them seem to be having fun and tries to ruin Peter’s big romantic moment.

2 When His Parents Pack Up All His Belongings

Season eight’s episode “Peter on the Couch” shows off both Chris Elliott’s acting skills and the most awkward aspects of Peter’s personality and tragic life. After the Barones have decided that they can take no more, Ray offers to drive Peter back home to his parents. However, when they get to Pennsylvania, it turns out that Mr. and Mrs. McDougall don’t want him back. They have already packed up all of his belongings and are planning on turning his bedroom into a prayer room.

1 And Even Boot His Beloved Miss Puss Outside

As if things couldn’t get any worse for Peter, he realizes that he can’t find his beloved cat, Miss Puss, among his belongings. As he becomes increasingly frantic, Mrs. McDougall confesses that they have put her outside, but, as Peter points out, again and again, Miss Puss is an inside cat. Tragically, Peter’s best friend appears to be his pet, and he is certainly more concerned about her safety than what is going to happen to him without a roof over his head.