‘The Office’ Romances, Ranked From Painfully Cringe to Soup Snakes
The beloved sitcom, The Office, tells the story of the folks working at a paper company called Dunder Mifflin in Scranton, Pennsylvania. Over the series’ 9-year run, many romances blossom under the office’s fluorescent lights. Some are sweet love stories, and some are so funny that we love to hate them. But, which coworker couples are good together, and which are the most toxic? Here’s the real ranking of The Office’s 15 office romances from worst to best.
15. Toby & Nellie
Poor Toby. (Paul Lieberstein) He really had an unfairly rough go of it. And, being half of the worst couple amidst some very bad couples is just another sad reality for everyone’s (except Michael Scott’s) favorite HR representative. When Nellie (Catherine Tate) arrives in the office and gives Toby some much-needed attention and an unexpected kiss, Toby thinks he’s finally found his match. Nellie, on the other hand, isn’t so crazy about the idea. And, Toby really, really can’t take a hint. This “couple” is just painful to watch. Too bad you can’t report HR to HR or Toby would’ve gotten a definite complaint filed against him for this relationship.
14. Pam & Roy
This office-warehouse love affair is an unparalleled mess. Roy (David Denman) doesn’t appreciate Pam (Jenna Fischer), at all, and she resents him for it. She cheats on him; they break up; they get back together; he starts breaking things when he finds out about the affair; they break up again. The two try to make their relationship work, but it was never a good coupling.
13. Jim & Karen
Some Office fans believe that Karen (Rashida Jones) was the right person for Jim (John Krasinski). And, sure – they could’ve had potential if he wasn’t completely in love with someone else (Pam). But, he was. And, he hid that from her, lied to her, and tried to use her to replace Pam, leaving her in the end. To quote Kevin (Brian Baumgartner), Jim gets “two thumbs down” for this whole situation.
12. Michael & Jan
Of all the couples on The Office, this one probably gives us the most laughs. And, while we all love laughing at them, this couple is way too toxic to condone. After some bizarre, erratic on-again-off-again back and forth, Michael (Steve Carell) finally admits that when he’s with Jan, (Melora Hardin) he’s unhappy. He ends things, but of course, he gets back together with her, because of her breast augmentation. Things, unsurprisingly, do not get better from there. So, while we may want to rewatch “The Dinner Party” over and over again, actually attending a dinner party with a couple like that… not so much.
11. Andy & Angela
Andy Bernard (Ed Helms) is certainly not a character who’s always in the right. Still, he was 100% the victim in his relationship with Angela (Angela Kinsey). Angela used Andy and led him on, all while treating him horribly and cheating on him. And, as bizarre and sometimes annoying as he can get, Andy really did love Angela and had the best of intentions when he was with her. It was a relief when he gave up on this relationship (even though it was mid-duel).
10. Andy & Erin
In the early days, Andy and Erin (Ellie Kemper) seemed like a perfect pair. There are periods of time during their back and forth and will they (again)/ won’t they (again) where it’s hard not to root for them. They’re two well-meaning weirdos who complement each other well – what’s not to like? Well, it all changes when Andy gets weird in a less fun and goofy way and a more disturbing way. Erin definitely deserved better, so it was great to see her get it.
9. Erin & Gabe
Angela may cruelly call Pam the “office mattress”, but Erin is the character with the most in-office relationships over her tenure at Dunder Mifflin. And, in the end, Erin breaks the heart of every guy who loses her. Gabe (Zach Woods) definitely fits that description. And, while the two were both sweetly awkward, this relationship wasn’t ideal for either of them.
8. Kelly & Darryl
Kelly (Mindy Kaling) and Darryl (Craig Robinson) really had potential. In one of Kelly and Ryan’s (B.J. Novak) many off-again periods, Kelly and Darryl get together. Darryl seems to really like Kelly, and Kelly is surprised by the way Darryl says “exactly what he’s thinking”. Still, Kelly, of course, uses Darryl to bait Ryan and ultimately cheats on him. It’s too bad, because if anyone was going to make Kelly (in Darryl’s words) “access her un-crazy side”, it was probably him (and definitely not Ryan).
7. Darryl & Val
In a warehouse love story, Val (Ameenah Kaplan) is another coworker who Darryl had serious potential with. These two were definitely cute together and probably could’ve made it for the long haul. But, Darryl wasn’t ready to settle down or prioritize her when it came time to move.
6. Erin & Pete
Pete (Jake Lacy) isn’t the most memorable or funniest character to grace Dunder Mifflin Scranton. But, by the time he gets together with Erin, it’s hard not to breathe a sigh of relief that the Andy/Erin romance has finally come to an end. And, Pete is the most solid match for Erin the office has seen, so all’s well that ends well.
5. Kelly & Ryan
Kelly and Ryan are the little unlikely office romance that could. No matter how many roadblocks get in their way, they always find their way back to each other. Sure, their relationship is painfully unhealthy and messy, and both of them are at fault for making it that way. But, there’s something sweet about the fact that these two just can’t quit each other. So, maybe they can make each other happy in the end (or at least they’ll continue enjoying their tumultuousness forever).
4. Jim & Pam
Ah, Jim and Pam — sitcoms’ royal couple. Jim and Pam gave Dunder Mifflin the slow-burn romance of the century. These two truly love each other and overcome many issues to make that love work. Still, there’s often trouble in paradise for these two. It’s hard not to wish that Pam got to live her dreams the way Jim did, and they aren’t always the “couple goals” they claim to be. Nevertheless, they do always end up working through their problems and fighting for each other, and that makes for a truly great pair at the end of the day.
3. Dwight & Angela
To be in a relationship both at the bottom of the list and at the top of the list is quite a strange feat, but that is typical Angela. (This woman has had two different sets of men duel over her…) Like Jim and Pam, Dwight (Rainn Wilson) and Angela are a long-running couple who started their romance way back in Season 2. These two are perfectly matched in extreme weirdness, antiquated values, and passion about some very strange issues. Their relationship is far from smooth sailing. But, there’s never any real doubt that these two are endgame. Despite trials and tribulations, affairs, paternity tests, and dead cats, Dwight and Angela were always destined to tie the knot at Schrute Farms and live bizarrely ever after.
2. Phyllis & Bob Vance
Sure, maybe Bob Vance of Vance Refrigeration (Robert R. Shafer) isn’t in the office, exactly, but he’s part of Scranton Business Park, so he’s close enough. And, these two are worth including, because they really are the “couple goals” the others strive to be. Bob treats Phyllis (Phyllis Smith) how she deserves to be treated – like the queen of the Pennsylvania refrigerator industry. He showers her with flowers on Valentine’s Day and never misses an opportunity to stand up for her. And, the two never stop having fun together, supporting each other, and having a (not-so-secretly) wild sex life.
1. Michael & Holly
Michael has his fair share of failed romances and suffers some serious pain as a result. Still, Michael and Holly’s (Amy Ryan) relationship proves that everything changes when the right person comes along. Holly is on Michael’s level with her humor and silliness in a way that no one else is. But, she also helps Michael become a better person by inspiring him to keep inappropriate jokes at bay, appreciate her commitment to ethics, and even reject his raunchy buffoon friend, Todd Packer (David Koechner). Michael and Holly understood each other deeply, made each other better, and had a blast doing it, which is what true love is all about.
