The American version of The Office is one of the most beloved sitcoms of the 21st century and helped to inspire countless other workplace comedies. One of the best shows to follow that trend is Brooklyn Nine-Nine which swapped out a paper company for a police precinct populated by similarly wacky characters.
The casts of these two shows share a lot of similarities and it’s clear that some of them would get along very well. But just as there are personalities that would click, there are also those that would clash in a major way. Whether they be romantic or platonic relationships, some couples from these two shows would work wonderfully while others would be disastrous.
Would Work: Toby & Boyle
It seems like every workplace comedy has those characters that are always the butt of the joke. For The Office, that person is definitely Toby, the dull HR rep who is treated so badly by everyone else simply because he is boring. And in Brooklyn Nine-Nine, Charles Boyle is often on the receiving end of the jokes.
While Boyle is liked a lot more than Toby, these two sad-sacks could bond over being outcasts. They each seem to have interests and personalities that most people can’t stand, but they would probably be very happy to be in each other’s company.
Wouldn’t Work: Gina & Toby
There are a lot of people who would not be able to form a connection with Toby, but Gina would be downright appalled by him. Even though she had a brief fling with Boyle, she would never allow herself to be attached to someone like Toby.
Gina has a very high opinion of herself and thinks she so much more interesting than everyone around her. On the other hand, Toby seems to be perfectly content being extremely uninteresting. If Gina had to spend more than a few moments with Toby she would likely die of boredom.
Would Work: Rosa & Darryl
In each of these workplaces, there are those tough characters with hard exteriors who eventually reveal a softer side. In the 99th precinct, Rosa Diaz can be very intimidating, rarely even smiling at even her closest friends. Likewise at Dunder Mifflin, Darryl Philbin is the tough warehouse manager who has no patience for nonsense.
But as tough as Rosa and Darryl seem to be, they have also proven themselves to be caring and thoughtful people. They would likely appreciate each other’s seriousness while also finding a deeper connection to their vulnerability.
Wouldn’t Work: Ryan & Rosa
Rosa might let her guard down among those closest to her, but people that annoy her are likely to feel the wrath of her anger. While there are a number of people at Dunder Mifflin who might get on her nerves, she would probably hate Ryan Howard most of all.
While Ryan started out as an unenthusiastic temp, he gradually became slimy and more insufferable as time went on. He is a morally weak person who still thinks he is better than everyone else. His hipster persona and false intellect would be so irritating to Rosa that he would be terrified of her.
Would Work: Holt & Oscar
In these workplaces filled with such crazy characters, surely the two most level-headed and intelligent people would form a connection. Both Captain Holt and Oscar fill these roles in their respective offices.
Holt is an effective leader whom Oscar would greatly admire, especially compared to Michael Scott. Meanwhile, Holt would likely be impressed by Oscar’s intelligence. They are also two people who enjoy culture and art in a more sophisticated way than those around them.
Wouldn’t Work: Terry & Dwight
While Holt is the leader of the precinct, Terry Jeffords is like the maternal figure. He is stern when he needs to be, but his main concern is with the happiness and safety of his team. Dwight also sees himself as someone whose job it is to protect the office, but he only really cares about the power he thinks that gives him.
Neither of these men would approve of the other’s approach to taking care of business. Dwight would see Terry as too soft while Terry would see Dwight as being antagonistic to the happiness of the office.
Would Work: Jim & Amy
Jim’s romance with Pam added a lot of charm to those early seasons of The Office. In Brooklyn Nine-Nine, the romance between Amy and Jake was very effective as well. So it makes sense that Jim and Amy would be an equally charming pair.
Much like with Jake, Amy would probably be annoyed at first with Jim’s immaturity but gradually see that he is good at his job and a sweet guy. For Jim, he would likely fall head over heels in love with Amy’s dorky personality immediately and pine over her for years.
Wouldn’t Work: Dwight & Gina
In both workplaces, Dwight and Gina are characters who see themselves as superior to the others. While one might assume that would make them an easy match, they would actually be terrible together.
Aside from their inflated self-worth, Dwight and Gina are drastically different people. His life on a beet farm, his love of science-fiction, and his colorless fashion choices would drive Gina insane. Likewise, Gina’s fascination with celebrity culture would seem pointless and childish to someone like Dwight.
Would Work: Pam & Jake
Just like how Jim and Amy would fit together, the other halves of those successful couples would probably be happy together as well. While they might be better suited to their partners from their respective shows, there’s a lot about Pam and Jake that works.
As with Jim, Pam would be charmed by Jake’s goofy and light-hearted approach to everything. Jake would also see Pam as the kind of down-to-earth and sweet person he needs in his life.
Wouldn’t Work: Michael & Holt
When looking at the two men who run these respective workplaces, Michael Scott and Captain Holt could not be more different. Michael is someone who can be effective at his job but needs to get all the nonsense out of his system. He would likely feel constrained by Holt.
Holt doesn’t like nonsense, but he puts up with it from his team so long as they do their jobs. But he would not have the same patience for Michael who is in a position of power. Holt would find him irresponsible and destructive.
