When The Office fans think of love in the office, they immediately think of Jim and Pam. Their relationship was a long-lasting storyline that fans couldn't get enough of. However, the next longest lasting relationship at Dunder Mifflin Scranton was between Dwight and Angela. No one's really sure when they started seeing each other (since they kept it a secret for so long) but even when they broke up, they were never really broken up.

Now, Dwight and Angela were real sticklers at work and rubbed many people the wrong way but they had some pretty loving moments together. But today, we're not looking at the happy times, we're looking at the worst things each person has done to the other within The Office's nine seasons.

ANGELA SLEPT WITH ANDY WHILE ALSO SLEEPING WITH DWIGHT

Dwight sleeping with angela – the office

The most hurtful thing Angela has done throughout nine seasons is play with the minds and hearts of two men she worked with. Since Angela is such a private person, she was able to sneak around without so much as raising an eyebrow. Not to mention Angela is very religious and praises good morals, so it was very out of character for her to be messing around with two guys (who loved her) at the same time.

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Granted, Dwight knew Angela was engaged to Andy when he started sleeping with her again but the only reason he continued doing so is that Angela told him he was the only man she was sleeping with. As we later find out, that was not the case.

DWIGHT TRIED TO GET OUT OF THEIR CHILD AGREEMENT

After everything these two have been through, Dwight decided he wouldn't mind having a child if its mother was Angela. The only logical way to go about this kind of thing is to create a child contract, right?

Although the two were no longer dating, they decided to partake on this journey of parenting together. Once Dwight realized he had feelings for Pam's cousin, however, he pulled the rug from under Angela and tried to break the contract. As you can imagine, Angela was pissed.

ANGELA LIED ABOUT THE PATERNITY OF PHILIP

The Office Angela Robert Dwight

Just like when Angela was engaged to Andy, she continued sleeping with Dwight during her courtship with The Senator (although not as frequently). However, when Angela found herself pregnant, everyone assumed it was her husband's.

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Things got sketchy when Angela delivered baby Philip prematurely and yet he was a perfectly healthy (and very large) baby boy. For months Dwight tried to find out the truth about the paternity of Philp and Angela denied it was his time and time again, insisting it was her husband's.

DWIGHT KILLED SPRINKLES...

Dwight gives Angela a cat in The Office

Just when things couldn't get any better between Dwight and Angela, she asked Dwight to check up on her sick cat, Sprinkles when she was busy. To her dismay, Dwight came back with some devastating news: Sprinkles was dead.

Now, in the back of Angela's mind, she had an inkling that Dwight killed her cat but he denied it. But later on, he admitted that Sprinkles was in pain so he put it out of its mystery. Understandably, Angela couldn't even look at Dwight for a few episodes until it was too much to bare and she broke up with him.

SO ANGELA RETALIATED BY HITTING DWIGHT

Angela from The Office holds up a photo of Sprinkles the cat.

Once Dwight finally admitted to killing Sprinkles, Angela acted out of raw emotion. It was in the middle of the Fun Run Michael was hosting to find a cure for rabies when Dwight told her he was a farmer, and as a farmer, it was his duty to put animals out of their mystery if they have no "utility."

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Since it was in the middle of the 5k, Angela continued to run faster until she stopped to hit Dwight. Now, we're not saying it was justifiable to kill her cat, but it's still not okay to hit someone. At least Dwight said he tried his best to make her go to sleep peacefully...

DWIGHT NEVER TOOK ANGELA IN AFTER SHE LEFT THE SENATOR

Angela and Oscar on the phone on The Office

Surprisingly, after Angela found out that her husband was gay and that he was sleeping with one of her best friends in the office, Dwight was her shoulder to cry on. He genuinely felt bad that he was cheating on her and that her marriage was a sham.

Oddly enough, he never offered her a place to stay when she was in a time of need. She was essentially living in a studio apartment with a baby and like, 10 cats when she was evicted and the only person who was there for her was the very same man who broke up their marriage: Oscar.

ANGELA INSULTED HIS BEET FARM AT THE DINNER PARTY

"Dinner Party" is hands down one of the best Office episodes out there. In an effort to have his co-workers see his updated condo (and life with Jan), Michael decided to throw a dinner party for couples only. With Jim and Pam, Angela and Andy, and Michael and Jan, the party was awkward AF. Things got even more awkward when Dwight rolled up with his former babysitter who he brought as his date.

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At the dinner party, Dwight was making a suggestive comment to Angela about his beet salad. "The thought of popping one of your beets into my mouth makes me want to vomit," she says dryly. Now, if you know Dwight, he takes his beet farm very seriously. At that moment, there was nothing worse Angela could have said to him.

DWIGHT MARRIED THEM WITHOUT HER KNOWLEDGE

As soon as Angela and Andy got engaged, Dwight was trying everything he could to break up the marriage. That's when he had the brilliant idea of offering his beet farm to Angela for the wedding, to show her what a beautiful land it was (and could be hers if she wanted it).

As Dwight is showing Angela and Andy the barn, he had a German minister conduct a "fake" ceremony for him and Angela. Unbeknownst to Angela, he had the two of them married in German so that she had no idea what was happening.

ANGELA GOT DWIGHT FIRED

The only person in the office we see Dwight going out of his way to help is Michael. He would do anything for Michel to prove how dedicated he is to Dunder Mifflin. However, when Angela messes up at work, Dwight covers for her and drops off the tax forms to corporate, which was two hours away.

Because of Dwight's tardiness without an explanation (and a few other things), Dwight was let go from Dunder Mifflin. Angela eventually comes to Dwight's defense so that he could get his job back, but it took her way too long to do so.

Although it was pretty messed-up of Angela to hide the fact that Dwight was the father of Philip, it's still her choice as Philip's mother to release that kind of information. He knew in his heart that the child was his and would do anything to get the results.

He decided to have family portraits done in the office and when the Senator changed Philip's diaper, Dwight took the diaper to a facility to have the DNA tested. Angela, of course, was outraged and chased him the entire way there.

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