For nine seasons we got to learn about the everyday lives of those working at Dunder Mifflin Scranton. As the regional manager for seven seasons, viewers saw how Michael treated his co-workers like the big family he always wanted. And while everyone in the office made fun of his antics and rolled their eyes at meetings, they were noticeably sad when Michael left.
Due to Michael's theatrical personality, he rubbed way too many people the wrong way, but he always found some sort of comfort in Pam. She made fun of him and vented about his actions to the camera crew but she didn't express the same emotions to his face (unlike Stanley or Phyllis). They were genuine pals whether she wanted to admit that or not. So, while these two didn't bicker as much as Michael and Toby or even Michael and Oscar, they definitely had their rocky moments...
WHEN MICHAEL DATED PAM'S MOM
Long-time viewers of The Office were elated when Jim and Pam tied the knot. But behind the scenes, we saw something else brewing: a romance between Michael and Pam's mom Helene. With the both of them bonding over heartbreaks, they seemed to hit it off... until Pam found out.
The thing about Michael is he doesn't understand boundaries. He wanted to find love and did would do everything he could to keep it — even if it means dating a co-worker's mother without talking to them about it first...
PAM INSULTED MICHAEL FOR QUITTING (BUT SHE DID THE SAME THING)
When Michael couldn't stand the direction Dunder Mifflin was going in despised working with Charles, he quit. It was a job move none of us viewers ever saw coming because we knew how much Michael loved Dunder Mifflin. Right after he quit and formed his own paper company (The Michael Scott Paper Company), Pam quit her job as a receptionist to being a whirlwind job as a salesman. However, once the Michael Scott Paper Company hit too many rough patches, Pam insults Michael for being so dumb. She insulted him for quitting the only job he ever loved but is she forgetting that she did the same thing?
MICHAEL (UNKNOWINGLY) SPILLED THE NEWS ABOUT HER PREGNANCY
Granted, Michael didn't know Pam and Jim were pregnant at the time he started this rumor, but it's the fact that the couple had to spill the beans early to their co-workers even though they weren't ready.
In this episode, the office has three new summer interns and Michael is tired of feeling like the odd man out. After hearing Stanley had an affair from the interns, he started spreading the news. But in classic Michael fashion, he felt bad for potentially ruining Stanley's life so he created more rumors to cover the original rumor — which is where Pam's pregnancy comes in. Thankfully, Pam and Jim dealt with the situation with class and admitted to being pregnant to save Stanley.
PAM REFUSED TO GO WITH MICHAEL DURING HIS SCOTT'S TOTS DEBACLE
In the sixth season of The Office, we learn about the worst thing Michael Scott has ever done. He promised an entire classroom that he would pay for their college tuition if they graduated high school on time. He called them Scott's Tots.
With graduation around the corner, it was time for Michael to come clean to his "Tots" about not having the money to pay for their tuition. He asks Pam to accompany him and she blatantly says no, saying "Michael, this is a terrible, terrible thing you've done." He continues to seek comfort from Pam and she refused to give it, which is why Erin went with him on his visit.
MICHAEL INSULTED HER WHEN SHE HAD HER GLASSES ON
When Pam and Jim first started dating, she showed up to work in a pair of her old glasses because she didn't have contact solution at her "friend's" house (aka Jim). She was already embarrassed to be wearing her glasses as it was but she felt worse when Michael called her ugly. But he didn't stop there. He said "Pam, in order to get hotter you need the glasses off. You're moving in the wrong direction." Thanks to Michael's brutal honesty, Pam tried forgoing her glasses, which made her job very uncomfortable.
PAM SLAPPED HIM IN FRONT OF THE OFFICE
Once Michael saw the light and realized dating Pam's mom was a bad idea, he broke it off with her...on her birthday. And while Pam was happy the two were no longer dating, she was even more mad at Michael for breaking her mother's heart. Michael apologized in his own way and asked what he could do to make the situation better with Pam. Her response? Hit him in front of everyone in the office.
Michael was clearly shaken up about the potential hit, and after she slapped him across the face, she admitted to Jim that it didn't feel the way she had hoped. Although we may want to hurt people for hurting us, two wrongs don't make a right.
MICHAEL AWARDED HER WITH 'LONGEST ENGAGEMENT' AWARD
To congratulate everyone on their hard work over the years, Michael loves to throw his own version of an awards show called The Dundies. However, this is n't a typical award show... For instance, he gave our Dundies for "Hottest in the Office," "Spicy Curry Award," "Diabetes Award," and more.
When Pam was still engaged to Roy, Michael gave them a Dundie for "Longest Engagement." While Roy thought it was hilarious, it only made Pam's reality that more depressing.
PAM FREAKED OUT ON MICHAEL FOR DATING HER MOM (IN A JUSTIFIABLE RAGE)
Truth be told, there weren't many times when Pam was mean to Michael. Was she sarcastic? Sure, but she's more or less motherly to him when he's on one of his antics.
As we mentioned, Michael dating Pam's mom was a real low blow, but for Pam to freak out as much as she did in the middle of the office seemed uncalled for. At the end of the day, both her mom and Michael are consenting adults. This was a manner that should have been handled privately with her mother there — not in the conference room, office, and parking lot of Dunder Mifflin.
MICHAEL PRETENDED TO FIRE PAM (AND MADE HER CRY)
In the first season, we get a taste for Michael's humor when he pretends to fire Pam... He calls Pam into his office and explains that the company is in a transition and that there will be downsizes made. To make his life easier, he says he has to fire her for theft (for stealing Post-It notes). She questions him and then begins to cry when Michael says he's not giving her severance for her time served at Dunder Mifflin.
It doesn't take a genius to see how immature and unprofessional this was. Especially when it's not even true!
PAM MADE HIM SIT IN THE BACK SEAT AFTER THE DIWALI PARTY
At Kelly's Diwali party, Pam decided to let loose and try to have some fun as a newly single girl. She seemed to be having a good time until the end of the night where she shoots Jim a text. She goes outside to get some fresh air and Michael joins her on the stoop. They both connect on being lonely and having a tough night; however, Michael saw this as an opportunity to shoot his shot with Pam. She (rightfully) turns him down and asks why he would do that. He genuinely apologizes and asks for a ride home, and instead of being understanding with Michael, she makes him sit in the backseat because she doesn't trust him.