The Office is known for some of the most uncomfortable humor on television, as it captures the day-to-day work lives of a group of people who work for the Dunder Mifflin paper company. During its nine-year run on NBC, the show featured plenty of cringe-worthy humor that fans still look back at with fondness–and trepidation–to this day.
Perhaps some of The Office’s best sources of awkward humor were its various relationships–many of which were too awkward for some fans to stomach. Certain The Office enthusiasts on Reddit have spoken up regarding which couples on the series were, in their opinion, simply the worst.
10 Michael And Helene
Reddit user esw97 believes that “Michael and Helene” are among the worst lovers in the history of the show. The couple was featured in a short-lived romance beginning after Jim and Pam’s wedding at Niagra Falls. The two would break up only four episodes later in the episode “Double Date.”
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This is perhaps one of the cringiest relationships on the show, mostly due to the fact that Helene is Pam’s mother. Pam lives through her worst nightmare as she is forced to grapple with the possibility of Michael Scott becoming her stepfather. And, to make matters worse, shortly after Pam comes to finally accept the relationship, Michael dumps Helene during her birthday lunch for being “too old.”
9 Andy And Erin
Redditor Right-Championship30 wastes no time in their response when asked which The Office couple is their least favorite, citing “Andy and Erin” as the worst relationship on the show. These two are both beloved The Office characters who were not included in the show’s pilot, who slowly came to develop feelings for one another, leading to a truly disastrous and drawn-out relationship.
Andy and Erin’s relationship became the primary love story following Jim and Pam’s wedding, as the two were set up as the next “it couple” for fans to follow. While the two were initially presented as quite a good match for one another, the final season of the series drastically changed Andy’s character, turning him into one of the worst boyfriends the show had ever seen, thereby justifying his getting dumped by Erin in favor of her new flame, Pete.
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8 Jim And Karen
HouseGinger voices a controversial opinion about Jim Halpert’s relationships outside of Pam Beasley, declaring that “Unless you were Pam, Jim was a terrible [boyfriend].” They specifically call out his behavior regarding Karen Filipelli, whom he unceremoniously dumped in order to be with Pam at the end of season 3.
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Jim and Karen’s relationship is often regarded as one of fans’ least favorite on the show, mostly due to the fact that most fans much prefer seeing Jim and Pam together. The couple did have its worthwhile moments, however, and many fans today realize that Karen had less to do with the relationship’s inevitable implosion than they may have thought upon their initial viewings.
7 Dwight And Angela
Commenting on a post suggesting that Dwight and Angela were one of the worst couples on The Office, lscandido added, “I don’t get how people like those two… they are both awful people to be in a relationship with. They both deserve each other though.”
Dwight and Angela had perhaps the most tumultuous relationship in the entire series, consisting of cat murder, multiple cheating scandals, an illegitimate child, and a babymaking contract that nearly got them both arrested. The final season of the series, however, greatly focused on both Dwight and Angela’s development into better people, leading up to their eventual reunion and wedding, which ultimately made for a great finale for The Office.
6 Pam And Roy
While listing their least favorite couples on The Office, extensionpanic8366 asserted that “Pam and Roy” were among the very worst in the show’s history. Many viewers will remember that the two are engaged at the time of the series pilot, though their longstanding betrothal would end in a nasty separation that destroyed their entire relationship.
Unlike many of the other worst relationships in the series, Pam and Roy were a couple specifically designed to be terrible. Roy was meant to be the romantic foil to Jim’s character, the exact opposite in every way. In order for fans to love the idea of Jim and Pam as much as they did, they had to first hate Pam and Roy even more.
5 Andy And Angela
Proper_Wishbone_4729 can’t help but find “Andy and Angela” to be one of the very worst couples the show has to offer in all its nine seasons. Primarily crafted as a way to get back at Dwight, Angela begins a relationship with his coworker that nearly ends in marriage, if not for the cheating scandal that breaks them up in season 5.
Though this relationship was truly one of the strangest mismatches in the show’s history, it did wonders for Andy’s character, who, over the course of his engagement to Angela, went from an annoying villain to a sympathetic personality that the audience could grow to love.
4 Angela And The Senator
HouseGinger believes that Angela and the senator, Robert Lipton, were a truly horrendous couple, writing “neither was faithful, he was cheating on her with her friend/coworker, and she let him think that Dwight’s baby was his, then deliberately lied to Dwight about it.” This is one of the few universally hated couples on the show that actually reached marriage–only for their entire relationship to come crumbling down in the midst of several clandestine affairs.
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This couple is particularly cringe-worthy given just how much the other characters on the show hate the thought of Angela and the senator being together. They routinely mock Angela for bringing up the senator (who they remind her is merely a state senator) and seem rather unsurprised by his infidelity. Ultimately, the couple’s grisly divorce came as a surprise to no one.
3 Erin And Gabe
“Erin and Gabe, definitely,” writes ThreeJC when asked who they believe to be the worst couple on The Office, “Erin never liked Gabe… [and] wanted Andy the entire time.” They also cite the fact that Erin forthrightly admits that she would have never agreed to go out with Gabe if she “didn’t have to.”
Erin and Gabe were a truly baffling couple that emerged seemingly from nowhere, used solely as a speedbump on the road to Andy and Erin’s similarly turbulent relationship. The two were mismatched in every way, making it no surprise that Erin calls it quits during Michael’s last Dundies ceremony. As if their relationship alone wasn’t enough, a future storyline includes the two engaging in a relationship post-mortem that proves to be one of the cringiest moments ever on The Office.
2 Michael And Jan
Redditor Klutzy-Bag-9206 correctly asserts that “Michael and Jan” are one of the worst and most toxic couples ever depicted in the comedy series. The two began as coworkers, later igniting a romance that drove the two to become the very worst versions of themselves, becoming one of the most joke-worthy couples in The Office.
Everything wrong with Michael and Jan’s relationship is encapsulated in the season 4 episode “Dinner Party,” where their houseguests are exposed to their toxic home environment. The two can’t seem to go more than a few minutes without fighting and genuinely seem to hate one another by the time the relationship is over.
1 Ryan And Kelly
BTBbigtuna lays down the truth when it comes to the very worst couple on The Office, claiming that the title could go to no one else. They write that the two are extremely toxic, as they “got married and divorced in a week, and even abandoned a baby in the last episode.”
Unlike any healthy couple, Ryan and Kelly seem to actively make each other worse people the longer they are together. While both seem relatively normal at the beginning of their relationship, both descend into selfish toxicity before long, making them a truly unsavory pair. In the end, they do end up together, though for how long is anyone’s guess.
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About The Author
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Jordan Iacobucci is an avid reader and movie fan, and has been since childhood. Jordan is known among his friends as the Marvel and Star Wars nerd, and even wrote a thirty-page college dissertation about Spider-Man! He is currently obtaining an English degree and lives outside Raleigh, North Carolina with his family. His other interests include working with children, reading, and music.
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