Running 188 episodes over nine seasons, The Office is still must-watch TV, over a decade after the first season aired. Thanks to a spot on Netflix, the hit show has found a new audience and become the subject of many binge watches and repeat viewings. Who would have thought that a half-hour comedy show set at a mid-level paper company would prove to be hilarious gold for years and years?
Along with its zany cast of characters, The Office has given us multiple relationships to mull over and dissect. In terms of main couples, there are many to choose from: Angela and Dwight, Michael and Holly, Pam and Jim, and even Phyllis and Bob Vance!
We figured it was best to go through all the couples we can think of – 25 to be exact – and rank them from worst to best. More than a few of these pairings were mismatched or began from, well, unsavoury origins, while others started out sweet and adorable before souring completely. We’ve done the hard work and rounded them up and ranked them accordingly, but we want to know if you agree with our decisions, or if you think another couple should reign supreme?
25 Toby Flenderson & Nellie Bertram
At the beginning of the series, Toby was a guy who was the office punching bag, especially for Michael Scott. He was a divorced dad of one who had a crush on Pam, but he was pretty harmless. As the series wore on, however, Toby got a little…unsettling. Perhaps it was his obsession with the Scranton Strangler, but his little love affair with a decidedly not-into-it Nellie made us cover our faces.
From the whispered sweet nothings to Nellie kissing him to get him to stop talking, this “relationship” was filled with secondhand embarrassment.
24 Oscar Martinez & Gil
Prior to the entire office learning of his orientation, Oscar was involved with Gil. In one episode, where Dwight stakes out Oscar’s home to see if he’s really sick, Gil and Oscar return from an afternoon of ice-skating. It’s cute but, honestly, there wasn’t a whole lot of spark between these two.
In fact, Oscar twice mentions that he’s planning to end things with Gil: Once in “Branch Closing,” where he says he’s “looking to get out of that relationship anyway” and in “Beach Games,” where he mentions planning to break up with him.
23 Michael Scott & Helene Beesly
The secondhand embarrassment was real with this relationship! Michael Scott has never been known for being the most tactful character on the show, but things hit a whole new level when he got involved with Helene, Pam’s mom.
Initially, these two were kind of cute together, but it all unravelled when Michael decided to break up with her on her birthday, after discovering her true age!
Then, in all subsequent interactions, he felt the need to remind Helene of his lack of feelings for her – even when she was meeting her granddaughter at the hospital! Yikes.
22 Oscar Martinez & Senator Robert Lipton
Any relationship that begins out of infidelity is going to be ranked low on our list, and Oscar and Senator Robert Lipton are no exception. Not only was Robert married to – and expecting a child with – Angela, but he was using Oscar to curry a minority vote while he was actually engaged in another relationship with his campaign manager! He unveiled it on live TV, naturally.
Kevin was the one who said it best when he called Robert out for being a terrible person, because the guy was bad news.
21 Angela Martin & Senator Robert Lipton
We had to put Angela’s relationship with Robert right alongside his unsettling relationship with Oscar – and rank both low – because he upended Angela’s life and left her contemplating living in a tent with her young son and whatever cats she still had.
When Robert and Angela first met, it was kind of cute, and he seemed charming, so we understand how she was taken in. Things went south quickly, though, and we grew to dislike him for being a barrier to Angela’s happiness for so long.
20 Kelly Kapoor & Ravi
Is it any wonder that so many of these one-sided, toxic relationships are resting near the bottom of the list for the worst relationships on The Office? Kelly Kapoor and pediatrician Ravi looked good together, but didn’t have anything in common. Even Jim stated that Pam had only introduced them to one another because they were both Indian.
Kelly enjoyed Ravi’s bank account and his ability to treat her to designer shoes, but his salary didn’t stop her from running off with Ryan once Ravi’s back was turned.
19 Dwight Schrute & Esther Bruegger
Nothing against Esther specifically, but she wasn’t Angela. She was a pretty young farm girl who seemed taken with Dwight, but she was also condescending. Remember her backhanded encouragement of Angela during the paper airplane contest, and advice that she use the prize money wisely? Yeah, we can’t blame Angela for flubbing that on purpose.
Esther was fine, but she didn’t have much personality, and we didn’t see the necessary chemistry between her and Dwight. We’re sure she’s happy elsewhere, with some other man who knows what an auger is.
18 Michael Scott & Donna Newton
Under other circumstances, we would definitely put Donna and Michael lower on our list, except that the kindling of their romance began with the introduction of Date Mike, so we have to give this pairing extra points!
Unfortunately, Donna was married, and put an unwitting (at first) Michael in the position of mistress. That she was happy to risk her marriage to a guy who seemed like a pretty nice person for Michael Scott is a little odd to us, but we’re glad Michael had the good sense to eventually pull the plug on things.
17 Kevin Malone & Stacy
Stacy, Kevin’s ex, gets more mentions than we actually see her. In fact, the character only appears twice, first in the episode “The Dundies,” in which she's sitting across the table from Kevin at Chili’s, and at the wedding of Phyllis and Bob Vance.
We know that Stacy has a daughter, whom Kevin brings to Take Your Daughter To Work Day, but not much is known about their relationship. Stacey ended things when they were both reading the paper one morning and that was it! Nothing too dramatic, good or bad.
16 Pam Beesly & Roy Anderson
Pam and Roy were just never meant to be. He never tried to be anything more for Pam, and rarely encouraged her. When he did do the bare minimum, like attend her art show, he expected praise.
These two seemed to be going through the motions for a long time, and Pam’s light and talent were snuffed out by Roy, who preferred a housewife to someone like Pam. For constantly selling herself short, and for Roy’s bouts of uncontrollable anger, these two rank low as a couple.
15 Jan Levinson & Michael Scott
When it comes to dysfunctional relationships, Jan and Michael have every territory covered. Unstable and selfish, Jan used Michael however she wanted without a care as to how that made him feel. She really seemed to lack any empathy for him, which was quite unsettling to watch at times.
Granted, we did get the fantastic episode “Dinner Party” out of it, where we got to see the true extent of Jan’s precarious behaviour. From “Serenity by Jan,” one of the candles made by her company that really doesn't have a pleasant smell, to how she possibly put toxins in the food, it's clear that no plasma TVs could keep this relationship going.
14 Erin Hannon & Gabe Lewis
A controversial choice perhaps, but Erin and Gabe weren’t terrible. In fact, when Gabe has everyone from the office over for his Glee viewing party, he really tries to make an effort as a couple, with homemade pizzas.
Of course, it wasn’t meant to be, and Erin publicly tells Gabe at The Dundies that she isn’t attracted to him and that she “[flinches] when [he] touches [her].” Gabe handles the breakup poorly, which gives us a chance to see him how Erin did, but there were some fleeting moments of sweetness between them, right?
13 Michael Scott & Carol
Played by real-life couple Steve and Nancy Carell, Michael and Carol were not a good pairing. The two initially met when Carol sold Michael his condo, and he began to pursue her, even having their first date at casino night in the warehouse. Later, he proposes to her after nine dates together and Photoshops his face onto a picture of Carol, her children and her ex-husband on a ski trip, which he then sends out as a Christmas card.
We can’t blame Carol for ending things then and there.
12 Jim Halpert & Katy Moore
Introduced in the final episode of Season One, Katy Moore (played by Amy Adams) was the attractive purse salesgirl who ended up casually seeing Jim for a few episodes. Katy was cute, perky and nice, but she had more in common with Roy than she did with Jim, from choosing Legally Blonde as a desert island movie to being a former cheerleader.
Their relationship was lukewarm, with Jim always pining for Pam, and so we can’t blame Katy for asking Jim why he even brought her on the booze cruise, which led to their inevitable split.
11 Darryl Philbin & Kelly Kapoor
Were these two a random choice? Yes. Did they kind of work together? Also yes!
Kelly is notorious for being high maintenance and a little bit nuts (it’s part of the reason she and Ryan kept finding their way back to one another). Darryl, on the other hand, refuses to buy into that idea and even tells her she needs to “access [her] un-crazy side.” However, this relationship seemed orchestrated by Kelly to make Ryan jealous, and even Darryl isn’t fazed when she ends things with him over text. In fact, he’s pretty thrilled!
10 Angela Martin & Andy Bernard
This relationship was a hard one to watch. From the knowledge that Angela was involved with Dwight throughout the duration of the relationship to Andy shadowing Jim’s proposal to pop the question, these guys were just mismatched. However, there were moments when Andy was quite sweet to Angela, from giving her Bandit (previously named Garbage by Dwight) to deferring to her on all wedding plans, he really tried to make it work. Angela, however, not so much.
We got good comedic moments from this couple, though!
9 Jim Halpert & Karen Filippelli
Look, it wasn’t Karen’s fault that her boyfriend was in love with someone else. In fact, when the two were in Stamford together, they were kind of cute, like when Karen competed with Jim in Call of Duty and won, and when she took him (and his bike) home after a night of drinking Jägermeister.
Things changed when they came back to Scranton, though, and tensions ran high with Pam in the picture. These two could have made it work if Jim wasn’t so hung up on Pam, but that wasn’t on Karen’s shoulders.
8 Darryl Philbin & Val
In the beginning, Darryl and Val were super cute together! She knitted him a “love beanie” and he got her some cashmere gloves (that he gave to Nate, but still). They had a “will they or won’t they” thing going on that was complicated by the presence of Val’s boyfriend, Brandon, but ultimately they did get together – and then, it was like things fell apart.
We learned that Darryl was trying to break up with Val – whom he worked so hard to win over – so he could be single when he moved to Philadelphia full-time.
7 Ryan Howard & Kelly Kapoor
Yes, these two were bad together. Yes, Ryan used Kelly for money, and Kelly was so hung up on Ryan it was ridiculous. That being said, they’re kind of like the accident you can’t look away from. These two were so imperfect for anyone else that they were perfect for each other!
Would they ever have a stable relationship? Absolutely not. Would it be filled with grand gestures and over-the-top dramatics? Definitely. Would we kind of love every bit of it? You bet.
6 Andy Bernard & Erin Hannon
Up until the final season, Andy and Erin are adorable. He tries to win her affections by literally gifting her with the 12 days of Christmas and recommending Disney films!
These two were sweet and innocent, and then it all went south when Andy decided to sail to the Bahamas with his brother, barely communicating with Erin throughout his three-month absence. He becomes a completely different person, really, and isn’t at all like the guy Erin (and we) fell in love with. We can’t blame her for running into the arms of our next entry.
5 Pete Miller & Erin Hannon
If things hadn’t soured so badly with Andy, we wouldn’t have had Pete, who truly seemed to want what was best for Erin. These two were on the same page for much of their relationship, and he won us over by reciting Die Hard in its entirety, proving he’s just as much of a nerd as Erin.
We don’t know if these guys ended up together, since they’re sitting apart at the panel in the final episode and we don’t see them dance together at Dwight and Angela’s wedding, but we were rooting for them!
4 Angela Martin & Dwight Schrute
Throughout their ups and downs, it was so good and wholesome to see Angela and Dwight end up together. This couple had passion and tenderness, and we’ll admit it – nothing gets us quite like Dwight shouting, “I’m a dad!” when Angela finally breaks the news to him, after over a year of waiting.
These two brought out the best in each other, and really seemed to care for one another, even when they attempted to just be friends. It’s difficult to say why they work together so well, but they do.
3 Phyllis Lapin & Bob Vance
We know that other couples in The Office get a lot of credit for being the best, but we think one of the most underrated of the bunch if Phyllis and Bob Vance. These guys are adorable together. Remember when Bob bid $1,000 for Crime Aid just to get a hug from Phyllis? Or how about when he – decked out in a full Santa Suit – came rushing into the office ready to defend Phyllis, who wanted to be Santa?
Plus, these two had a lot of passion, which was occasionally exhibited to an uncomfortable degree!
2 Michael Scott & Holly Flax
After trying – and failing – to find love so many times, it was sweet and unexpected to see Michael and Holly together. Rather than try to cover up his weirdness or quirks, Michael could be himself.
In fact, she was as big a dork as he was! Together, they understood one another on a level like no one else. After all, she was able to find him around Scranton simply by knowing what he was likely to be doing. Learning that they later married and had children – which both had always wanted – was the icing on the cake.
1 Jim Halpert & Pam Beesly
Some may think they’re overrated, or that Jim changed in later seasons, but Jim and Pam were endgame from day one. These two operated on a different level. They knew everything about one another and still managed to grow as a couple, and as parents. Sure, they had some difficult times in Season Nine, but they got through them, with compromise and communication.
It was a real reflection of how relationships – even seemingly strong ones – take work to maintain, and for that reason, and their undeniable cuteness and chemistry, they are number one on our list.