All the Office Romances in ‘The Office,’ Ranked

‘I just want to be friends. Plus a little extra. Also, I love you’
All the Office Romances in ‘The Office,’ Ranked

At a rest stop halfway between Scranton and New York City, Jim gets on one knee with a small box in his hand as rain pours down from the sky. He extends the box forward to his completely shocked future fiancée and says, “I couldn’t wait. Pam, will you marry me?” Cars roar by as Pam holds her hand to her mouth, eventually letting out a “Yes,” and the two embrace. Despite the unspectacular setting, this is the moment all the fans of The Office had been waiting for ever since the Jim and Pam love story began five seasons earlier.

While Jim and Pam are one of the greatest couples in TV history, they’re far from the only romantic duo on The Office. The Scranton branch of Dunder Mifflin served as a workplace and a love nest for several employees. Sometimes for the better; sometimes for the way, way worse. Which is what we want to get at the heart of today — the couples that worked versus the hot messes. (Note: We’ll only be looking at Dunder Mifflin employee pairings, which means overlooking ones like Phyllis/Bob Vance, Vance Refrigeration and The Scranton Strangler/Necks.)

So let’s get to ranking these relationships from purely toxic to beautiful love story…

Ryan and Kelly

Time Together: On and off for all seasons

Toxic or Romantic: Purely Toxic

Bad for emotional and mental health but great for TV, Ryan and Kelly are equally broken, selfish, narcissistic and incapable of change. They show their affection for one another only through huge romantic gestures reserved for rom-coms couples about to run away together. Unfortunately, every minute that follows is torture. Her endless talking, his endless scheming and their inability to agree on anything make this romance a Valentine’s card abandoned in a Chernobyl level of toxicity.

Erin and Gabe

Time Together: A couple of months

Toxic or Romantic: Very Toxic

Hilariously wrong for each other in every way and a fruitful source for cringe, Gabe and Erin were a surprising choice for each other. Gabe dominates every conversation and movie night with the creepy charm of a haunted house innkeeper, while Erin seems to go with the flow due to severe abandonment issues from being in foster care at an early age. A complete stranger could see that these two have little to nothing in the romance department, and no matter how many Nike tattoos Gabe gets, Erin will never be the “it” that Gabe was “just doing” ever again.  

Pam and Roy

Time Together: High school (not shown) to Season Three

Toxic or Romantic: Very Toxic

Displaying the passion of an after-school special, it was clear that Pam and Roy didn’t have much chemistry. He was far too comfortable standing still in every aspect of their relationship, and she was clearly looking for that spark that she once felt in the hopes it would return. It didn’t. When Pam officially left Roy, it was a celebration for the fans that she was finally sticking up for herself while also facing her fear of being alone. This broke the codependency cycle of their relationship and created a newer, better Pam Beesly, who set her sights on what she truly wanted: Jim Halpert.

Michael and Jan

Time Together: Three Seasons

Toxic or Romantic: Very Toxic

As explosive as a Michael Scarn movie trailer, Michael and Jan are toxically codependent, with very little communication happening. And when they do articulate their issues, hide your plasma screens because the Dundies start flying. They are two people who appeared destined to ruin each other’s personal and professional lives, but somehow both made it out better than they started. It seems like Jan and Michael were each other’s rock bottoms, leading both to finally climb their way out.  

Andy and Erin

Time Together: Three Seasons

Toxic or Romantic: Toxic

It took a few tries for the timing of Andy and Erin to sync up in the love department. Small flirtations led to massive gestures, including the live recreation of the “12 Days of Christmas,” which basically consisted of around 30 live birds. What’s interesting about these two is when things started to get settled in their courtship, each physically ran away. Andy ran off with his brother on a three-month voyage with the family boat, while Erin took what she thought would be a permanent trip to Florida for the new Sabre store. Deep down, it feels like they both knew there wasn’t much substance to their connection beyond their dorky good vibes. Like cheap bubblegum, the flavor only lasted so long.  

Darryl and Kelly

Time Together: A few episodes

Toxic or Romantic: Toxic

As expected, a quick rollercoaster that went up fast, then plummeted down and ended exactly where it started, with everyone getting off and no one getting hurt. Darryl was actually a nice fit for Kelly for a while. His natural chill demeanor balanced her Real Housewives energy, and his honesty instantly disarmed her. However, Kelly’s inability to love anything but drama and anyone but Ryan is what ultimately destroyed this relationship, which Darryl happily accepted.

Jim and Karen

Time Together: Season Three

Toxic or Romantic: Toxic

Their relationship was really mid. Meeting during Jim’s transfer to Nashua, they had a fun fling that helped Jim get over Pam’s initial rejection. However, the merger and subsequent move back to Scranton revealed many holes in communication and highlighted Jim’s general disinterest in any other women besides Pam. They rank lower on this list due to their general lack of chemistry and their breakup being reminiscent of a middle school dance. 

Andy and Angela (and Dwight)

Time Together: Season Four

Toxic or Romantic: Toxic

This love triangle was created when Angela began sleeping with her “ex” lover Dwight Schrute during her engagement to Andy. Dwight having zero issues being the “other man” and adamantly declaring his love gave Angela all the motivation she needed. However, that changed once the affair was revealed to Andy and the entire office. During their duel, Andy and Dwight would come to learn that Angela was, in fact, actively sleeping with both of them. It led to the pair striking up a friendship and abandoning her wholesale. This stays low on the list due to Angela’s dishonesty, Dwight’s deceit and Andy’s pure dumbness.

Darryl and Oscar

Time Together: Season Nine, Episode 15

Toxic or Romantic: Kind of Romantic

Though it was all a ruse to get a couple’s discount, Darryl and Oscar were a couple for at least a few minutes. When denied their justified right to a Valentine’s Day price reduction at a nail salon, they supported one another, immediately vocalizing their mutual disgust to the owner and leaving in a show of solidarity for the LGBTQ+ community. Despite their relationship being just a cover, they would be the most interesting dinner conversation on this list by far.  

Andy and Angela (Sans Dwight)

Time Together: Seasons Four and Five

Toxic or Romantic: Semi Romantic

With his persistence, quick thinking and musical talent, Andy finally won over Angela and began dating her soon after Angela and Dwight had broken things off. He was a very safe choice and easy to please because Andy himself is a desperate people-pleaser. On paper, they should work and be able to satisfy one another’s needs, but they lacked any spark entirely due to Angela’s disinterest in pretty much everything that is Andy Bernard.  

Erin and Pete (aka Plop)

Time Together: Season Nine

Toxic or Romantic: Pretty Romantic

Fun, light, energetic and hot, Pete and Erin rank higher on this list than most familiar couples since they could genuinely enjoy each other’s company while still getting to know one another on a deeper level. Despite the massive wedge attempt by Andy in hiring both of their exes, they were able to weather the storm while not pointing fingers at one another. Instead, they maintained a warm flirty vibe all the way to the end.  

Dwight and Angela

Time Together: On and Off Seasons Two through Season Nine

Toxic or Romantic: Romantic 

An easy third place here, as their love story is long, complicated and beautifully weird. Even early on, they’re a clear match for each other, both stern and dominating in their demeanor, leading to an adoration spawning a playfully sweet relationship. When presented with the conflict of Dwight murdering Angela’s cat by putting it in the freezer, they break up but maintain a healthy level of respect for one another until eventually reuniting. Their wedding was a great cherry on top of this twisted sundae, as it incorporated everything we love about the two weirdos.   

Jim and Pam

Time Together: End of Season Three to Season Nine

Toxic or Romantic: Very Romantic

The fairy tale prince and princess of Dunder Mifflin, Jim and Pam reign high on this list as they hit all of our couple goals. Sweet, sincere, with a long history of romantic gestures and inside jokes, PB&J (Pam Beesly and Jim, by Kevin Malone) is one of the best couples Scranton has to offer. They’ve shown their highs and lows throughout the series, remaining near the top of this list due to their long-burn love story and genuine commitment to their marriage and family. However, they’re not ranked number one due to a lack of transparency on Jim’s behalf when he started his Philadelphia company (which everyone hated). Jim and Pam’s inability to support one another during this period showed an immaturity in their relationship that was only bested by one other couple…  

Michael and Holly

Time Together: On and off for a couple of seasons

Toxic or Romantic: The Most Romantic

The beautiful love story that follows all the steps of the Jim and Pam fairy tale: Guy loves girl, girl gets transferred due to an intentional corporate shuffle, girl dates another coworker, guy gets girl transferred back and girl finds the love of her life waiting for her with a ridiculously colossal ring and a barrage of crazy unsafe marriage proposals. 

Michael and Holly were made for each other, and it was clear as day from her early episodes on the show. With their obvious kismet and connected dorkiness, the Scott/Flax relationship is incredibly sweet and endearing to anyone who feels like their time to find someone has passed. But sometimes, the game of love is chess, not checkers, as Michael and Holly have an openness and maturity in their relationship that a younger Mr. Scott would have sunk. Michael’s instant support of Holly’s parents and his selfless act of leaving his home, friends and career behind to be with her makes them the number one couple in the electric city.   

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