Based on the BBC series of the same name, the American version of The Office hoped to bank on the same popularityy of the original series. With many new faces and even writers for the show, the series slowly became a staple in NBC’s weekly lineup.
Centered around the mundane lives of the office workers of the Dunder Mifflin Paper Company, the series explored not just office life but the lives of each worker as well. Through heartbreaks, love, and the everyday occurrences at work, The Office managed to create a series full of heart, humor, and real characters that audiences grew to love. Though the series lost its lead actor, comedian Steve Carell, by seeason 7, the series continued through two more seasons. Fans everywhere bid a tearful goodbye to The Office on May 16, 2013, with happy endings for most of the characters.
Throughout the series, most characters, whether central or recurring, had their fair share of either blossoming love or eventual heartbreak. Over time, the office workers found themselves dating each other and even found love outside of the walls of their office building.
While some couples made us swoon and envious, others made our stomachs turn, hoping they would end as soon as possible. In this article, we will explore the pairings from the show that helped improve the quality of the series and also contributed to its lowest moments.
From the relationships we cheered for to the ones we outright booed, here are 10 Couples That Hurt The Office (And 10 That Saved It).
Hurt: Darryl Philbin and Kelly Kapoor
Any relationship on The Office involving Kelly Kapoor would be expected to be drama filled and ridiculous. However, after her breakup with Ryan, she took a chance with Darryl Philbin from the warehouse.
In a sharp contrast to her previous relationship, Darryl never put up with Kelly’s ridiculous behaviors or attempts to play games.
The biggest issue with this relationship was that it was all a farce.
Kelly simply used Darryl to try to make Ryan jealous. Although they did share some cute moments, this relationship simply had no legs to stand on. We all knew Kelly would make it back into the arms of Ryan eventually and Darryl happily accepted their breakup.
Saved: Michael Scott and Jan Levinson
Amidst the over-the-top relationships from the show, Michael and Jan certainly stand at the top of the list. This ridiculous on-again, off-again relationship started with a messy kiss in the parking lot of Applebee’s in “The Client” and led to their first hookup in Sandals, Jamaica.
Their toxic relationship brought plenty of entertainment and included numerous vasectomies, Jan’s firing, and a disastrous dinner party. Even after breaking up, Michael still found himself still trying to be a part of her life through her pregnancy.
However horrible this relationship was, it served as a lesson for Michael for future loves. By enduring such an awful experience with Jan, he was able to discover what true happiness actually felt like.
Hurt: Dwight Schrute and Esther Bruegger
When Dwight wasn’t actively pursuing a relationship with Angela, fans witnessed a few near relationships for Dwight over the years. Although we still regret that some of the other never played out (sorry, Isabel), his pairing with Esther never seemed like a possibility.
After inheriting his aunt’s beet farm, he entered into a relationship with Esther thanks to her father.
Although Esther appeared to show genuine interest in Dwight, we all knew he was not meant to be with her.
With Angela’s relationship with the Senator finally crumbling, Dwight saw yet another opportunity to be with her and his son. Even on the day he planned to propose to Esther, he chose to propose to Angela instead (finally).
Saved: Darryl Philbin and Val Johnson
Darryl always remained a fan favorite throughout the seasons of The Office. Although we saw his career blossoming over the years, his relationship status remained pretty limited.
Besides a brief reappearance of his ex-wife Justine and his messy time with Kelly, his love life stayed very stale. However, with the appearance of new worker Val, Darryl finally finds someone to pursue an active relationship with.
Between their back and forth flirting and his declaration of interest in Val (despite having a boyfriend), fans grew to love the dynamic between the two characters.
Though the relationship was short-lived, we finally got the chance to see Darryl in a healthy relationship for once. In the end, Darryl reconciled with his ex-wife and moved with her and his daughter to Austin.
Hurt: Jim Halpert and Katy Moore
As a fan of The Office, it has been hard for anyone to see characters Jim and Pam with anyone else other than each other. With the appearance of Katy in the episode “Hot Girl”, we thought maybe Jim would find someone to be with.
Referred to as the “Pam 6.0”, she ignored the advances of Michael and Dwight, opting for Jim instead.
Though they seemed to have some chemistry, Jim eventually realized he had little in common with her and knew very little about her. She simply served as a distraction from his feelings for Pam.
He broke up with her during “Booze Cruise” after Roy finally announced he was setting a date for his marriage to Pam.
Saved: Jim Halpert and Karen Filippelli
After his failed attempt to win Pam’s heart in “Casino Night”, Jim relocated to the Stamford and found new hope with Karen. Although she was nothing like Pam, the two seemed to click very well together.
Able to keep up with Jim’s silly humor and pranks, Karen felt like a good fit for the heartbroken Jim and served as a good partner for him.
Granted, things got complicated when they chose to move to Scranton, but they still tried to make their relationship work. However, the presence of a newly single Pam began to affect Karen negatively. Jim realized his feelings for Pam were too strong and eventually broke up with Karen.
Hurt: Michael Scott and Helene Beesley
Another of Michael’s many irrelevant relationships was his odd and brief relationship with Helene Beesley, Pam’s mom. Fans still don’t understand why this pairing came about and would like to forget it.
Their relationship just served to drive Pam into an angry frenzy just for the sake of comedy. Even Michael wasn’t very invested in the relationship since he didn’t even know how old Helen really was. In fact, upon discovering her real age, Michael immediately began to lose interest in her.
This mismatched pair didn’t contribute much to the overall story of the show nor did it result in anything worthwhile. Well, unless you count Helene being dumped by Michael on her birthday as eventful.
Saved: Pete Miller and Erin Hannon
While soome fans wanted to see Erin’s relationship with Andy work out, she seemed to find a better pairing with new worker Pete. Although the interest between the two began while she was dating Andy, she soon discovered that her feelings for Pete were too strong to resist.
When Andy selfishly left to go on a very long boat trip with his brother Walter, Erin recognized how caring an attentive Pete has been to her.
Upon Andy’s return, Erin finally ended things with Andy for a much healthier relationship with Pete.
They soon became the new “Jim and Pam” and possibly stayed together through the series’ finale.
Hurt: Toby Flenderson and Nellie Bertram
We are still trying to comprehend why this matchup ever happened. Two of the oddest characters on the show being brought together on a, what, a whim? Honestly, it was just uncomfortable and pretty darn gross.
Their love match began in “Here Comes Treble” when Toby finds himself attracted to Nellie because she came to work in a Toby costume. After their strange kiss during the episode “Dwight Christmas”, fans became quite confused about their “relationship”. Although Nellie seemed to have forgotten about the kiss, Toby hadn’t, being noticeably more affectionate toward his coworker, thinking they were now together.
Thankfully, this pairing didn’t last long, and Nellie soon found herself repulsed by Toby, much like most of the office. Thank goodness!
Saved: Ryan Howard and Kelly Kapoor
How could you not love the train wreck that was Kelly and Ryan? Granted, these were two of the most selfish characters on the show individually, but together they became a force to be reckoned with.
These two lovebirds continued their on-again, off-again relationship through the entire show.
Between the constant breakups, attempts at making the other jealous, and even a quickie marriage, Kelly and Ryan continued to come back to each other.
Even after the two seemed to finally end things (Kelly moved on to Ravi and got engaged), they still managed to drift to one another once again. With Kelly abandoning her fiancé and Ryan abandoning his baby, they run off together in the season finale.
Hurt: Roy Anderson and Pam Beesly
Though her relationship with Jim served as the endgame for the series, we were introduced to Pam through her time with Roy.
Roy was insensitive and often neglectful, but this pairing did help Pam see how much better her life would be with Jim. Given that their breakup was a necessity, their spiraling relationship together eventually took a turn for the worse.
This pairing hit a new low after their breakup when Roy lost his temper in a bar. His anger continued into the office when he attempted to attack Jim. This act seemed a bit excessive, turning fans against Roy for good.
Saved: Andy Bernard and Erin Hannon
Honestly, we were rooting for this couple to make it. They shared the same silly energy and instantly clicked when they were together. Andy’s courtship of Erin even included gifting her “The Twelve Days of Christmas” in real life, a plan bordering on being both insane and romantic.
After initially ending things, they both tried to move on with other people. However, in an attempt to rekindle their relationship, Andy drove down to Tallahassee, Florida to confess his love for her.
Unfortunately, is decision to take a three-week cruise with his brother, leaving Eric behind, seemed to be the last straw. She eventually broke up with him after he returned and moved on to Pete.
Hurt: Oscar Martinez and Robert Lipton
For the first three seasons of The Office, Oscar appeared to be in a relatively healthy relationship with his boyfriend, Gil. Along the way, the couple eventually broke up, as mentioned in “Beach Games” when Oscar declared he might “try women for a while."
Sadly, the writers decided the next relationship for Oscar would involve a closeted gay man who was the fiancé and future husband of his coworker, Angela Martin.
This relationship was messy from the start, with Oscar knowingly participating in Robert’s infidelity.
Despite his past issues with Angela, this type of betrayal should have never happened between these friends. In the end, the Senator not only cheated on Angela but Oscar as well.
Saved: Bob Vance and Phyllis Lapin
Among the many failed relationships and awful hookups, Phyllis and Bob maintained one of the healthiest relationships on the show.
Shown to be dating as early as season 2, the two eventually settle down and get married, serving as an excellent antidote for the typical Michael Scott antics. Their marriage continued to be quite healthy, despite some concerns Phyllis had of Bob cheating on her with his secretary. However, her concerns are quickly dismissed by Dwight, and she pushed her doubts aside.
They confirmed to be still very much in love during the “Blood Drive" episode where they sneak off to a bathroom stall together during a Valentine’s Day lunch with Pam and Jim. Yikes, but also, aww!
Hurt: Andy Bernard and Angela Martin
To be fair, Andy had a genuine interest in Angela at first and did what he could to win her over. Although Angela dismissed his affections for her numerous times, she eventually broke down and gave in. However, she secretly began her affair with Dwight again, despite committing to marrying Andy.
At times, Angela seemed to have doubts about the affair and appeared to want to care about Andy. In the end, however, the relationship was revealed, with Andy being heartbroken over the betrayal.
Angela’s selfishness led to her losing both Andy and Dwight, in the end. Fans were sad to see kind-hearted Andy put through so much pain.
Saved: Dwight Schrute and Angela Martin
This long-standing affair carried on for the majority of the show and remained a fan favorite throughout the series. Since the reveal of their secret affair, Dwight and Angela seemed like a mismatched couple. However, over the years, the two came to appreciate their differences and even began to complement each other.
Through breakups, a baby contract, and misunderstandings, they still managed to come back to each other.
Fans longed for the day that the two would eventually get the timing right and finally be together. Thankfully, the series ended with their marriage. Dwight and Angela finally able to be a happy family with their baby.
Hurt: Robert Lipton and Angela Martin
The relationship between Angela and the Senator seemed wrong from the start. Understandably, fans longed for Angela and Dwight to get together, however, the termination of their baby contract served as the end of their affair. Hoping to find true love elsewhere, she began dating Robert, and they eventually get engaged and married.
In a twist of fate, she became the oblivious spouse in a marriage where her husband was doing the cheating with her coworker, Oscar. She remained in the union, too ashamed to admit she made a mistake and unwilling to be humiliated.
In the end, Angela suffered far more than she should have and her time with Robert seemed like unnecessary filler for her storyline.
Saved: Michael Scott and Holly Flax
There wasn’t anyone on The Office more deserving of a healthy and happy relationship than Michael Scott. Though often his fault, his years of dealing with awful girlfriends, selfish lovers, and brief affairs left him yearning for something more. Looking to have a happy life with his future wife and kids, Michael finally found his match with Holly Flax.
These two characters shared the same quirky behaviors and proved to be a perfect match.
Despite some hiccups in their relationship (and eventual breakup), the two managed to make their way back together when Holly returned to Scranton. Their engagement scene, though comical, became one of the sweetest moments of the show’s history. They eventually married, with Michael revealing in the series finale that they had a family together.
Hurt: Gabe Lewis and Erin Hannon
When you take one of the most lovable characters on The Office and pair her with one of the most despised, you get one of the most worthless couples on the show. Erin’s time with Gabe came after her breakup with Andy and he presumably served as her rebound.
With the pressure of Gabe being her boss, she went along with the relationship.
However, she remained unhappy the whole time as she found him repulsive and their relationship to be quite boring.
After she finally broke up with him during “Michael’s Last Dundies”, Gabe went to great lengths to win her back, including threatening Andy. His obsession with her turned very creepy and, in the end, we were just happy to see him go. Their ridiculous relationship added nothing to the show and just became an annoyance.
Saved: Jim Halpert and Pam Beesly
Possibly the most beloved couple on the entire series, Pam and Jim’s relationship became the heart of The Office. Starting from a crush in season 1, this couple went through hell and back just to be together. Thankfully, their story didn’t end there as we watched the couple date, fall in love and eventually marry.
Their friendship, dynamics, and playful nature made them one of the most beloved couples on television.
Fans around the world were devastated when their solid marriage began to crack under the pressures of Jim’s new job and the task of making their relationship work long-distance. However, the couple made an effort to solidify their marriage and began to repair their relationship.
Who’s your favorite couple on The Office? Let us know in the comments!
