The 8 Best and 8 Worst Relationships on The Office

The Office is one of the best shows that has ever been on TV. The episodes make you laugh and make you cry and, after nine seasons, we have fallen in love with the characters. We became so incredibly invested in the characters' lives and, of course, their relationships. And with a show running that long, it is bound to have some amazing couples (and also some truly terrible ones), but no matter what, we all have strong opinions about them.

The Office is known for having inter-office relationships. A lot of the time it seems like everyone in the office is paired up with one another. Sure, there are a lot of people who have relationships outside of the office, but a huge portion of the characters are in relationships with people they work with.

Is there any office on earth that has this many couples? My guess is a really big "no", unless it is a family run business. I mean, lots of sitcoms couple up their characters, so it isn’t like this is too far fetched, but this is overkill. So here is a list of both the best and the absolute worst couples this show has to offer.

16 Best - Erin and Pete

Via: NBC

The new, younger, debatably hotter version of Jim and Pam. Pete is the new guy in his twenties, and his smile brings joy to women everywhere. Together they are goofy and fun loving. Their relationship was just adorable, and definitely the best relationship that Erin had with anyone in the office.

15 Best - Daryl and Kelly

Via: Youtube

I wish this couple lasted longer, to be honest with you. Daryl was so stable, so down to earth, so rational, and most importantly, so honest. I love Daryl, and I just want him to be happy. He is easily one of my favorite characters on the show. And doesn’t Kelly deserve someone so rational? Doesn’t she deserve someone who is so honest with her? Unfortunately, Kelly didn’t want that.

While they were together I think Daryl brought out a better side of Kelly. She wasn’t lying and telling people she was pregnant. She wasn’t looking for attention while she was with him. Perhaps most importantly, she was super supportive of him.

14 Best - Michael and Carol

Via: Reddit

Okay, the real reason I put this one in the best column is simple - Carol is his wife in real life, and it is just hilarious that she played this role. Honestly, I think they could have been a kind of good relationship had Michael not been going through something.

13 Best - Jim and Karen

Via: Just Jared

Was this the best relationship? No. But I think we say that because we have literally been rooting for Jim and Pam since Pam fell asleep on Jim’s arm in the conference room. So did we give Karen a fair chance? No.

There was a part of me that really wanted Jim and Karen to work out. If it wasn’t going to work with Pam, then why couldn’t he find happiness with someone else? Also, I think when Jim left for Stanford, I was mad at Pam. Like, why didn’t she tell Jim that she canceled her wedding for him? Was he just supposed to know that after she denied him twice?

12 Best - Phyllis and Bob Vance

Via: Buzzfeed

Bob Vance and Phyllis have one of the most solid relationships on the show. They have a longer relationship than anyone else in the office and there is only one time that Phyllis wonders if Bob was having an affair; which ends with Phyllis laughing about how ridiculous it sounds. Plus, they have passion, that is for sure. So much so that they even leave their lunch with Jim and Pam to have sex in the restaurant’s bathroom.

11 Best - Dwight and Angela

Via: NBC

It could be argued that this is one of the best-suited couples in the entire show. They were together long before Jim and Pam. Their personalities are so compatible that it just makes sense that they were together. To imagine either of them with any one else simply doesn’t work. It was as if everyone else they ever dated was just a place holder until they finally got back together.

What this couple fell short on was the fact that they never wanted to be public. Before Dwight killed Angela’s cat, they snuck around, never telling anyone in the office that they were together. Then, when Angela was with Andy, they were sneaking around again. That just doesn’t seem all that healthy.

10 Best -Michael and Holly

Via: Fanpop

After years of seeing Michael with Jan, who is arguably the worst person on the show, it was so nice to see him with Holly. It was like; he finally found his counterpart.

Michael is an interesting character. A huge part of the time, he is insufferable. He says things that aren’t just stupid, but sexist, racist and homophobic. But there are times when you wonder if he just generally has no idea that the things he is saying are bad because beyond how insufferable he is, he is a really kind and caring guy who would do anything for those that he loves (even if they are kind of out there and no one asked for them).

9 Best - Jim and Pam

Via: Hollywood

I know, what a shocker to put these two as the best couple on the show. But you know what, I didn’t make this list to shock people; I did it for accuracy and for what I believe to be true.

Jim and Pam have been through it all. They have given hope to office relationships all over the world. Even years after the show has ended, they are still used as the standard that people hold relationships to. And do you know why? Because it is so real. Their love wasn’t hot and heavy, or on and off for a number of years. Did it take forever for them to get together? Yes. But to be honest, it was that much more satisfying when they got married.

8 Worst - Erin and Andy

Via: Fanpop

They’re nice people. There’s nothing wrong with them as human beings. But this is one of my least favorite relationships on the show. Was it the absolute worst one? No, there are couples that are actually cringe worthy. Ones that you watch, and you just ask yourself, why?

7 Worst - Erin and Gabe

Via: Youtube

It’s not like they are the worst couple in the world, but they are just really ill-suited for one another. And I really don’t love Gabe, to be honest with you. I think they do this as like a teaser for Andy and Erin because it is clear that they still like each other, but I’m not into it.

6 Worst - Angela and Robert

Via: Youtube

Yes, they met in a cute way. But the second time we are introduced to Robert, Oscar informs us that he is gay. And yeah, we can’t take one man’s judgment over another's sexuality, but then we see him checking out Ryan’s butt. Yeah, that’s pretty clear evidence. And then there is the fact that Angela is so insufferable about him being a State Senator. Like, he is a State Senator and she is treating him like he is a Senator who works in DC - he isn’t.

5 Worst - Kelly and Ryan

Via: Boston Magazine

Is this the worst couple in the office? Absolutely not. But they are insufferable for sure. Ryan, at first, isn’t all that bad. He is kind of funny and he makes some witty observations about his coworkers. But as soon as he gets the promotion to corporate, he becomes one of the most obnoxious people on the show - especially after he loses it all and comes back as a temp. And then there is Kelly; sweet, talkative, annoying, and not really self-aware. To be honest, I just always feel bad for Kelly when it comes to Ryan.

These two are on and off more than the lights at Dunder Mifflin. I feel like Kelly just wants to settle down with Ryan, and he just sort of strings her along. He breaks up with her when he goes to corporate. He makes her break up with Daryl when he comes back. And then he just leaves her to go to what he says is Thailand, when he is really in Florida.

4 Worst - Michael and Helene

Via: Post Grad Problems

For those of you who have forgotten who Helene is, it’s Pam’s mom. Yeah, you read that right, Pam’s mom. Are you cringing yet? I want everyone to take a minute and pretend that you work at Dunder Mifflin, and Michael Gary Scott is dating your mom. Yeah, it’s awful, and I truly empathize with Pam.

It would be one thing if Michael and Helene just hooked up at Jim and Pam’s wedding, it would still be awful, but it wouldn’t be nearly as terrible. The fact that they are dating, and like, actually trying to have a relationship makes it oh so much worse.

3 Worst - Angela and Andy

Via: Cleveland

Guys, why were they ever together in the first place? What a terrible match. Their personalities were so far from one another that it isn’t even a case of "opposites attract." These are opposites that shouldn’t be friends or even acquaintance at that.

What’s annoying about this couple is that Angela only agrees to date him to get back at Dwight. And then, sweet, dumb Andy decides to propose the same day that Jim was planning to ask Pam to marry him - which is infuriating. Also, it’s like super soon for him to ask her to marry him, which makes me cringe. Then, while they’re engaged, Angela sleeps with Dwight the entire time.

2 Worst - Pam and Roy

Via: Just Jared

At first, you don’t like them together because you think that Jim and Pam are meant to be. Of course when you want two people together, and one of them is in a relationship with a guy who isn’t nearly as good as the other, you want them to break up. But with Pam and Roy, it is so much more than that.

Roy is one of the worst boyfriends of all time. He doesn’t listen to Pam, and basically, it leads to her emotionally cheating on him with Jim. They’re engaged, but there are no plans for them to actually get married for years. This relationship is one of those things where two people who have been dating forever stay together because they are afraid to be alone - even if they aren’t meant to be.

1 Worst - Jan and Michael

Via: Fanpop

This is easily the most toxic relationship on the entire series. First, Jan is Michael’s boss, and she was always mean to him, even before she became single. One of the first episodes she is in, he is telling the camera how awful of a boss she is - so why would he want to be with her?

Even while they are dating, Michael doesn’t have that many good things to say about her. He spends a whole episode talking to all the ladies in the office about how terrible she is. For me, the really telling episode was when they invite the other couples over and have the worst dinner party in history. Watching it makes me uncomfortable to this day. And then, to make matters worse, she throws him under the bus when they have litigation against Dunder Mifflin; thankfully this is finally when Michael decides to end it with Jan.

Sources:  Fandom, Buzzfeed.

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

The 8 Best and 8 Worst Relationships on The Office