The Best Office Romances: Ranking The Relationships On The Office

As a prickly kind of antagonist of the happy-go-lucky character Jim, Dwight Schrute had many contentious relationships with his coworkers throughout the duration of The Office. But he had a much less contentious relationship with Pam’s friend Isabel Poreba:

Dwight hooks up with her ahead of Jim and Pam’s wedding, and they later end up making out despite Dwight having a “pre-natal contract” with Angela.

While some fans didn’t like the headstrong Isabel, we enjoyed seeing Dwight find a little affection. Almost as much as we enjoyed the introduction of a new character who wasn’t afraid to stand up to the ever-prissy, borderline tyrannical Angela.

As a handbag saleswoman, Kate Moore was a very minor character in The Office, but her performance was quite memorable because she was played by big-screen legend Amy Adams.

Many fans disliked the character because she was basically written as the opposite of Pam, right down to her vapid tastes in entertainment (Legally Blonde is her “trapped on a beach” movie) and how easily she managed to bond with Roy (something Pam could never quite do).

Jim dumping her after Pam and Roy announce their wedding date was always inevitable, but she played an important part in helping his character realize that he’ll never be able to settle for anything less than Pam.

While The Office became famous as a sitcom, it was never afraid to borrow a few soap opera tropes, especially when it came to the relationships characters were a part of. This was on full display when Angela began dating a state senator who was a closeted gay man, going so far as to get married and give birth to his child, only for the politician to have a secret affair with Oscar. 

From a distance, the entire plot sounds completely insane. However, we enjoyed how much it revealed about both the social aspirations of Angela (who would later divorce him after serving as his trophy wife) and Oscar (who gets dumped as soon as the senator comes out of the closet).

The relationship on The Office between Oscar and his longtime partner Gil is one that we see very little of, but these rare appearances helped us to learn more about our favorite characters.

For example, there’s a running joke early on that characters like Dwight and Michael don’t recognize the very obvious signs that Oscar and Gil are gay lovers and not simply friends or roommates.

Oscar ultimately ends up breaking up with Gil in season 5, and after Gil was particularly savage about Pam’s artwork (infamously calling it “motel art”), many fans weren’t too sad to see him go.

While it’s known for its over-the-top comedy and plots, there are certain character relationships in The Office that hit closer to home than we could have predicted.

For example, Andy and Erin never seem to settle into a real groove as a couple, and there are reasons for that: Erin is hopelessly naive about many things and Andy is a pompous idiot with anger issues.

Their breakup was one that fans could see from a million miles away, but depending on your patience threshold for these characters, their courtship could be pretty fun to watch. And it’s all a bit less awkward when you rewatch the show.

If you’ve ever worked in corporate life, then you may know that The Office is weirdly accurate in its range of character archetypes. Ryan and Kelly both play the kind of vapid, “too cool for school” younger works every office environment has, so it was no surprise that they ended up hooking up.

What was hilariously surprising is that the show was true to both of their characters: because each person is a toxic and self-centered jerk, they kept finding new ways to hurt each other and then hook back up, with everyone on the show and in the audience wondering why this creepily-captivating couple doesn’t simply break up.

While we all grow up hearing that “opposites attract,” the writers of The Office clearly understand that it’s usually similar personalities that end up in compatible relationships.

That’s likely why Dwight and Angela ended up together: each character is extremely controlling and more Type A than Elon Musk, so these two characters that hardly anyone else in the office can even stand ended up getting together.

It was a genuinely crowd-pleasing moment watching them get married in the series finale of the show, and we’re guessing Angela must really love Dwight since she didn’t treat him putting her cat in the freezer as a relationship-ending red flag.

Here’s a hot take that will probably have fans of The Office yelling at us: even though Karen was added to the show to force Jim to confront his feelings towards Pam, she ended up having better chemistry with him than Pam ever did.

It helps that Karen is an ambitious woman who wants to get the most out of life, and she deeply wanted to have a romantic partner who was equally ambitious.

However, Jim chose fan-favorite character Pam instead, forever signifying that he will choose whatever is safe and familiar rather than taking a real chance on a new love and a new life.

While they never bring it up very explicitly in The Office, the truth is that Holly ends up being the kind of unicorn character that Micahel could previously only dream of.

In previous seasons, we saw Michael consistently crash and burn with different women in large part because none of them knew what to make of his bizarre and often childlike sense of humor.

Holly came into his life like a force of nature: she laughed at his strange jokes, joined in his strange pranks, and eventually joined his life when the two of them finally decided to get married.

Don’t act surprised: everyone who has so much as seen a preview for The Office could tell you that Jim Halpert and Pam Beasley were going to end up the top pick for the best relationship on the show. We got to see their romance grow for nearly a decade, from goofy early flirtations to a show-stopping wedding and then major adult decisions like buying a house and having children.

And while the show sometimes forgot what to do with their relationship (the less said about that boom mic guy and Pam, the better), Jim and Pam’s love is so strong that it remains major #relationshipgoals for fans around the world.