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Every "The Office" Relationship, Definitively Ranked

"I feel like all my kids grew up, and then they married each other."

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23. Michael and Jan

NBC

OK let's be real — Michael and Jan were the absolute worst. Sure, maybe they had a nice trip to Sandals, Jamaica (lol), but the rest of their relationship was a disaster. Jan was crazy and controlling, and Michael just let her walk all over him. Let's not forget the dinner party meltdown or her making Michael get three vasectomies. Snip snap snip snap snip snap!

22. Dwight and Esther

NBC

Guys, Dwight and Esther was just never gonna work. At this point, he and Angela were so meant to be, it was absurd. Oh, and let's not forget Esther's dad trying to trick Dwight into buying a tractor with him. Despicable.

21. Erin and Gabe

NBC

Erin and Gabe... bleh. Erin admitted it herself that she was not even slightly attracted to him. This whole relationship was also painful because Andy was so in love with Erin. Let's not forget when Gabe and Erin hosted a Glee viewing party and Andy ate powdered seahorse and then threw up in Gabe's bed. Erin's iconic Dundies break-up was the perfect way to end this awful relationship.

20. Nellie and Toby

NBC

Ohgodohgodohgod, this was WEIRD. First, they hooked up because Nellie was dressed up AS TOBY. Plus, Toby's inability to read any kind of signals made this an awkward mess.

19. Kelly and Ryan

NBC

Where to begin with these two? In some ways, they were perfect for each other in the sense that they are literally insane. But how many times did these two have to break up and get back together before they realized they were not meant to be? They still didn't learn their lesson in the very end, when they ran off into the sunset together: Ryan, abandoning his BABY, and Kelly abandoning her incredibly handsome doctor boyfriend.

18. Angela and Robert

NBC

Sure, Angela and Robert met in a really cute way during Dwight's Hay Carnival. But then there's that little catch that Robert was secretly gay and had multiple affairs, including one with Oscar. These two continued their sham of a marriage for far too long, making this one of the worst relationships.

17. Jim and Katy

NBC

Let's not forget that Jim briefly dated Katy, the purse saleswoman. When Jim first asked her out, we felt happy for him, since it was a sign of him moving on from his hopeless crush on Pam. Katy, however, turned out to be shallow and awful, and the two had a painful breakup on the booze cruise.

16. Pam and Roy

NBC

Sure, it's easy to automatically hate Roy because he's not Jim, but Roy wasn't ~all~ that terrible. So he wasn't a good boyfriend and he wasn't supportive of Pam's art, but he did have his sweet moments. Remember when they reconciled at Phyllis' wedding? So cute. What WASN'T cute was when he wrecked the bar and then tried to attack Jim in the office.

15. Michael and Helene

NBC

This was an odd pairing for sure, yet they were sweet together for a short period of time. They both bonded over their sadness and loneliness at Pam and Jim's wedding. On Helene's birthday, Michael made her a nice gift and set up a thoughtful lunch. Too bad he decided to dump her right afterwards because she was "too old."

14. Dwight and Isabel

NBC

This little fling suuuuure was a head-scratcher. Isabel was initially more into Dwight than he was in her (?!?!?!) but he then later realized she would be an excellent candidate to have his child. Unfortunately for Isabel, Dwight had a contract to have a baby with Angela. This relationship probably could've turned into something if it wasn't for that contract.

13. Kelly and Darryl

NBC

"Darryl Philbin is the most complicated man that I have ever met. I mean, who says exactly what they're thinking? What kind of game is that?" Good ole rational Darryl would've been great for crazy Kelly. These two probably would've been a good couple, however it just wasn't meant to be. This was probably best for Darryl.

12. Michael and Carol

NBC

Michael and Carol seemed like a good, solid couple. They dated for a while, which was a bit shocking, since Carol seemed so reasonable. Sure, it was weird of Michael to propose to her at Diwali, but if she decided to settle for him, they probably would've been a solid couple.

11. Oscar and Robert

NBC

Possibly the most controversial relationship on the show, because we couldn't help but be happy for Oscar and sad for Angela at the same time. It was nice that Oscar found love, but it was heartbreaking when the senator turned out to be cheating on Oscar as well.

10. Kelly and Ravi

NBC

I WILL NEVER FORGIVE KELLY KAPOOR FOR LEAVING THIS BEAUTIFUL MAN. Ravi was a smart, handsome, patient doctor and Kelly left him for RYAN, of all people. Like Darryl, Ravi balanced out Kelly's crazy and somehow didn't get impatient with her. "Big mistake. Huge."

9. Angela and Andy

NBC

This was a strange couple, but for some reason, we all liked it. It started sweetly, with Andy offering Angela a stray cat and serenading her over a conference call with his a capella troupe, Here Comes Treble. Andy was nothing but sweet to Angela after she continued to be cold and unfaithful. If it wasn't for Dwight, these two could've made it.

8. Jim and Karen

NBC

Now before everyone gets upset, remember: We cannot hate Karen. She fell for Jim before she even knew that Pam existed. She was a good girlfriend, and really cared about Jim. They had tons of cute moments, like when Karen drove drunk Jim home from work, or when they did the beach games together. Yes, Jim was meant to be with Pam. But we can't hate Karen. If Pam didn't exist, everyone would be Team Karen.

7. Darryl and Val

NBC

Darryl and Val were completely adorable. There was the perfect amount of drama and buildup when Val was still dating Brandon, and there was that intense face-off and reading of text messages (dot dot dot dot dot). And when Val showed up in a gown to the office party, so Darryl showed up in a tux? So cute.

6. Erin and Pete

NBC

These two seemed like a perfect match. Both sweet and goofy, Pete and Erin had really good chemistry. Pete was there when Andy decided to leave on a three-month boat trip, and the two really bonded.

5. Andy and Erin

NBC

Though he royally screwed it up in the end, Andy and Erin were a beautiful couple. They both loved each other so much, and it was painful to watch when they wanted to be together, but weren't. Their first date was so sweet: she and Andy just watched TV with her weird foster brother because Erin was sick. Let's not forget Andy's loving, yet misguided, idea to give her the 12 Days Of Christmas for secret santa. And when he drove all the way to Florida to get her back? True love.

4. Phyllis and Bob Vance, Vance Refrigeration

NBC

Phyllis and Bob were legitimately Scranton Business Park's ultimate power couple. They were so in love, sometimes disgustingly so (remember Valentine's Day in the restaurant bathroom?) and joined together the two most important businesses in the building: Dunder Mifflin and Vance Refrigeration.

3. Dwight and Angela

NBC

Dwight and Angela were the perfect couple. They first got together under mysterious circumstances in Season 2, and only broke up because Dwight killed beloved Sprinkles. The two never, ever stopped loving each other. Even when they weren't together as a couple, they continued to engage in lots of warehouse meet-ups and even made a contract to have a child together. They eventually did have little Phillip, and it was an utterly beautiful moment when Dwight found out he was the father.

2. Jim and Pam

NBC

These two obviously are near the top of the list, and for good reason. They are an absolute perfect match. They had such an incredible friendship that romance was the next logical step. Sure, they had some rough patches (let's just block out Season 9), but they always came back to the fact that they loved each other so much. Jim and Pam's Niagara Falls wedding was perfection, and they have such a beautiful little family. "When you're a kid, you assume your parents are soulmates. My kids are gonna be right about that."

1. And Michael and Holly

NBC

Finally, Michael found the one he was meant to be with. From their very first meeting, you could tell Michael and Holly were soulmates. They were both so loving and goofy; such a welcome change from mean and controlling Jan. Even after they were separated, Michael knew he just had to wait and that one day he and Holly would be together again. These two are soup snakes. 💕

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