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The 8 Best and 8 Worst Relationships on The Office

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The 8 Best and 8 Worst Relationships on The Office

Via: Boston Magazine


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

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.

Unlike with Gabe, there is an instant chemistry between these two, and unlike with Andy, they don’t take forever just to get nowhere. It was Pete who picked up the pieces when Andy left on his three-month boat trip, in one of the most selfish acts that have ever been recorded in a fictional relationship. So we were happy when Erin and Pete got together because we were hoping that finally she would actually be with someone who loved her and would give her the family that she never had.

15. Best – Daryl and Kelly

Via: Youtube

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.

And then Kelly threw that all away just to be with Ryan again. I will never forgive her for this.

14. Best – Michael and Carol

Via: Reddit

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.

I think that while Michael was seeing Carol, he was having sort of a crisis. He wanted to be married and have kids, and he forgot about the fact that he had only been dating her for a couple of weeks. So of course, in true Michael Scott form, he proposes to her extremely early in their relationship. Then, as if that wasn’t bad enough, he crudely pastes his face over her ex-husband’s in their family photo of a ski trip the previous year, and sent that out to his family and friends as a Christmas card. This relationship was basically doomed from the get-go, but it definitely wasn’t his worst relationship.

13. Best – Jim and Karen

Via: Just Jared

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?

To be honest, I felt bad for Karen. She moved to Scranton for Jim, and she didn’t even really know why he left there in the first place. She didn’t know his history with Pam and it just didn’t really seem fair to her.

12. Best – Phyllis and Bob Vance

Via: Buzzfeed

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.

What keeps them from being higher on the list? We don’t know that much about them as a couple, to be honest. We know that Bob is extremely protective, and comes off pretty strong. We also know that they basically stole everything from Pam’s wedding with Roy – which isn’t cool at all. While they have a solid relationship, to steal what someone else planned for their wedding is a dick move for sure.

11. Best – Dwight and Angela

Via: NBC

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.

In the end, they found each other, and that’s really all you can ask for. Weirdos and mean people need love too, and Angela and Dwight are a perfect example of that.

10. Best -Michael and Holly

Via: Fanpop

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).

So it wasn’t like we didn’t want Michael to find happiness – just the opposite. To find someone like Holly, who is like the female version of Michael, was nothing short of incredible. I love this couple because together they are just ridiculous.

9. Best – Jim and Pam

Via: Hollywood

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.

And it isn’t like they are too perfect either so that it is unbelievable. They go through real issues that normal human beings go through. I love this couple so much that I wish the actors who played them were married in real life.

8. Worst – Erin and Andy

Via: Fanpop

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?

With these two, it just takes so long for them to get together, and not in a good way. Often times, sitcoms will prolong relationships in order to draw them out and make them more satisfying for the viewer. But with these two, I don’t feel that at all. They never seem to connect, and when they actually do, there’s nothing there. I just don’t understand why Andy doesn’t move on accordingly, he pines after her for so long that it is just infuriating when it amounts to nothing.

7. Worst – Erin and Gabe

Via: Youtube

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.

The way this relationship starts is that Erin claims she had to say yes when Gabe asked her out because he was her boss. Dude, that is not a good reason to say yes when someone asks you out. She isn’t really attracted to him, they aren’t cute together, and I just don’t see any chemistry at all here. When he makes her a romantic Valentine’s scavenger hunt it leads her right back to Andy. When she broke up with him at the Dundies, there was universal rejoicing from fans everywhere, and it will go down in history as one of the best breakups of all time.

6. Worst – Angela and Robert

Via: Youtube

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.

But here’s the real kicker – Robert cheats on Angela with Oscar, which is a huge scandal and breaks up their marriage. It is kind of ridiculous that they even get married in the first place, and then the whole time Robert is sleeping with Oscar. It’s so far away from what anyone would consider a healthy relationship, just one in a long line of bad relationships for Angela.

5. Worst – Kelly and Ryan

Via: Boston Magazine

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.

While they keep things interesting, they are so far from a good couple by any standard of a healthy relationship.

4. Worst – Michael and Helene

Via: Post Grad Problems

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.

What makes this even more unbearable than it already is, is how Michael handles it, much like how he handles all relationships. He went into this one hot and heavy – in true Michael style. But then Michael finds out how old she is on her birthday, and while at lunch for her birthday he freaks out and breaks up with her, proving just how shallow he is, and how much chaos he can cause not only in a relationship but in the office as well.

3. Worst – Angela and Andy

Via: Cleveland

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.

So while this relationship was pretty much doomed from the get- go, it only got worse as it went on, and it succeeded in making viewers hate Angela even more.

2. Worst – Pam and Roy

Via: Just Jared

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.

What makes them truly terrible is when they get back together after the wedding is canceled and Roy loses his mind when he finds out Jim and Pam kissed. His reaction is extremely violent. What would happen if they got married and she upset him? Would he turn violent towards Pam? I’m glad she left before we ever had to find out.

1. Worst – Jan and Michael

Via: Fanpop

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.

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