Michael and Jan have one of the most notoriously awful relationships on The Office. This relationship was doomed from the start, considering that Jan never really like Michael all that much combined with Michael’s disrespectful personality. On top of that, their working relationship was awful, too, and their relationship likely would have broken many company rules. Both of them did some pretty awful things to each other when they were together, and their relationship was extremely unhealthy.
Here are the five worst things John did to Micahel, and the five worst things Michael did to Jan.
MICHAEL: HOW HE DISRESPECTED HER WHEN SHE WAS HIS BOSS
When we first meet Jan, she is Michael’s boss. He is extremely disrespectful of this position from the start. First of all, he’s just bad at his job and never really listened to her. Secondly, as they started to develop feelings for each other, he makes a ton of inappropriate comments. He crosses so many lines of professionalism and keeps trying to turn their relationship romantic and sexual even when Jan says she isn’t interested in taking things further. The way Michael acts towards her in a business setting is quite appalling.
JAN: GETTING A SPERM DONOR WHILE THEY WERE DATING/MAKING MICHAEL GET VASECTOMIES
One of the weirdest and strangest things that Jan does while they are dating is to get a sperm donor to get her pregnant even when she is dating Michael. This is especially awful seeing that Michael wanted to have kids.
She didn’t even tell him she was doing this, and she was trying to have a child that wasn’t his. Plus, she also made Michael get multiple vasectomies even though he didn’t want to. She was extremely controlling of what he did with his body and then went behind his back to have a baby.
MICHAEL: SENDING OUT THE PICTURE FROM JAMAICA TO THE ENTIRE COMPANY
Michael’s inability to be professional about their relationship was a huge problem from the start of their relationship. After Jan agrees to go with him to Jamaica, he ends up sending out the picture of her to the entire warehouse staff. While this might have been an accident, the fact is that he was trying to share this intimate picture of Jan topless with Todd Packer. This was inappropriate, and Packer would have been sure to share it around anyway.
JAN: MAKING HIM SLEEP ON A SMALL CHEST AT THE END OF THE BED
The dinner party episode of The Office is one of the most well-known for being hilarious because of how absurd it is. This episode shows just how dysfunctional and unhealthy the relationship between Jan and Michael is. There are multiple red flags here, such as the fact that Jan doesn’t let Michael spend his money on things he wants and basically takes over his entire house even though she doesn’t really contribute to anything. But, the worst thing she does is make him sleep on a small chest at the foot of their bed. This is definitely an abusive thing to do.
MICHAEL: WHEN HE GOT BACK TOGETHER WITH HER BECAUSE OF HER BREAST AUGMENTATION
In a shockingly mature moment, Michael ends up breaking up with Jan because she doesn’t make him happy and makes him uncomfortable in the bedroom. But, then two weeks later, he is happy to get back together with her purely because she gets a breast augmentation.
Michael is totally willing to get back together after seeing this, and it’s clear that the thing that matters to him the most is how Jan looks.
JAN: WANTING HIM FIRED EVEN WHEN THEY WERE DATING
One of the strangest things about their relationship is how awful Jan was about Michael even when they were dating. She was still his boss for part of the time they were dating, but even still, she only had negative things to say about his work performance. While Michael was definitely difficult, it doesn't make sense to date someone who you think is horrible in so many ways. This just goes to show how Jan was always rather disgusted by Michael more than anything else.
MICHAEL: INVITING BOTH HER AND CAROL TO CASINO NIGHT
Michael is one of the most careless and inconsiderate characters on the show. He’s terrible at relationships, and he’s not good at treating people well. While he didn’t mean to invite them both as Jan first turned him down, the way he acted when they both showed up was so awkward and uncomfortable. He treated them both like they were conquests and didn’t know how to just be friendly and respectful to both of them.
JAN: THE DEPOSITION
During the deposition when Jan is trying to sue Dunder Mifflin for firing her, the way she treats Michael is truly awful. First of all, she makes him tell her version of events even though he’s uncomfortable with being in that position.
But, the worst thing is when she brings his diary to use as evidence without telling him. It’s quite a betrayal to take something so private without even asking for permission.
MICHAEL: HOW HE DISRESPECTED HER WISHES AFTER THE FIRST TIME THEY KISSED
When Michael and Jan first kiss in a Chili’s parking lot, Jan later insists it was a mistake. For a long while, she doesn't have any interest in taking things further, but Michael doesn’t listen to this. He keeps trying to hit on her and push their relationship. The way he is so unprofessional about this and continues to disrespect her is really hard to watch.
JAN: ASSAULTING HIM
While Michael did some pretty horrible things to Jan while they were dating, Jan really takes the cake for being the worst. It’s implied multiple times that Jan would cross Michael’s lines during their sex life. He clearly would say no to certain things, and she wouldn’t listen. This is definitely assault, and it’s truly disturbing that this was going on.