Jan Levinson and Michael Scott had a professional relationship on The Office until they kissed each other in season 2's 'The Client.' While Michael wanted more from that moment, Jan wanted to forget it ever happened and was harder on Michael at work because of it.
By the time season 3 rolled around, Jan gave in to her feelings and started dating Michael. They had a rather chaotic and toxic relationship until they broke up in 'Women's Appreciation.' But as was the case for these two, they got back together until one final blowout fight in one of the cringiest episodes, "Dinner Party." Up until this point, multiple reasons led to their breakup.
A Constant Power Struggle
Due to Jan's position at Dunder Mifflin, it was hard for her to be anything but CEO at home. She didn't know how to shut off being a businesswoman when she was home alone with Michael. This created a power struggle between the two.
Michael felt dominated and not respected at home or in his relationship. He was very much a person who appreciated equality in a relationship and at work, but Jan made that impossible to happen. Instead of Michael, Jan should have ended up with Robert California.
Jan As A Stay-At-Home Girlfriend Wasn't Working For Either Of Them
When Jan was fired from her job at corporate, she left her life in Manhattan and moved in with Michael in Scranton. When Jan first ran the idea by Michael, the look on his face said it all — he knew it wasn't a good idea.
Instead of looking for a job, Jan lived off of Michael, slept in, and focused on drinking. Jan living as a stay-at-home girlfriend was not working for either of them. Michael should have given Jan some business advice during her time of need but he seemed scared of her.
Their Differing Views On Kids
In "The Client," Jan said one of the reasons why she divorced her husband was because she wanted kids and he didn't. Michael has always wanted kids so this news was a positive one for his relationship with her.
But as viewers found out in "Dinner Party," the two had been fighting about children for a while. Michael had three vasectomies due to their indecision, which led to a heavy toll on their relationship. In the end, they decided not to have kids, but Jan did look into sperm donors during their time together, which was a low blow for Michael.
How They Started Dating
Jan and Michael's relationship timeline started after they went to Jamaica together. Once they were back from their trip, Jan realized she should act on her feelings for Michael and see how it went.
However, since they started their relationship in secret and due to how controversial it was because Jan was Michael's superior, they did not start the relationship off on the right track.
Jan Was Embarrassed To Be Seen With Michael
One of the saddest things about Michael is how embarrassed Jan was to be seen with him. in 'Cocktails,' the two went to their first business outing as a couple. While Michael was excited to show off his girlfriend, Jan didn't want to be seen with him.
Michael is a fan of public displays of affection while Jan hated it — especially in front of her colleagues. On the car ride home, Jan itted that their relationship was a mistake and things were better when they were a couple in secret. Her embarrassment of his true self was a huge reason why they couldn't work.
Their Sexual Activities Made Michael Uncomfortable
One of the reasons why Michael liked Jan so much in the beginning is because he was attracted to her. Michael threw inappropriate jokes at her but they were constantly ignored by Jan and met with a sigh.
When they started dating, it became clear that Jan's sexual needs were different than Michael's. In 'Women's Appreciation,' Michael said how much he enjoyed cuddling with Jan and scrapbooking, but Jan was more interested in videotaping their rumps and then rewatching the footage to criticize his form. This was entirely unhealthy.
Michael Couldn't Be Honest With Her
Jan had no problems being honest with Michael because of her need to be in control. Michael, on the other hand, did. It didn't make sense that Michael felt like he couldn't speak his mind in his relationship since he had the upper hand (she moved into his house and lived off his finances, after all), but he didn't.
It wasn't until Michael talked to his female colleagues that he had the confidence to end things with Jan. He wasn't honest with her about money, his hatred for her treatment of him in public, and his disapproval of the sex life.
They Weren't Open About Finances
Michael had one of the highest salaries at the Scranton branch but it wasn't as much as maybe other managers within the company. Michael didn't like conflict and was comfortable the way things were. However, when Jan moved in, his salary couldn't both of them.
Jan started redecorating his apartment, which cost Michael a fortune. Sadly, he never told her that he couldn't afford it. Instead, she ran them both into debt. A financial conversation needed to be had but never happened until Michael declared bankruptcy.
All Of Their Cracks Were Exposed In Dinner Party
The cracks in Jan and Michael's relationship were exposed in "Dinner Party." After inviting Jim, Pam, Andy, Angela, and Dwight to their house for dinner, it became clear that they couldn't stand each other. Jan took over Michael's house and made it a place where he wasn't comfortable.
The guest rooms became her office and workspace, and she made Michael sleep on a bench at the end of their bed. Their friends saw their relationship crumble at the end when Jan threw Michael's Dundie at the TV. After that night, the two broke up and Jan moved out.
Jan's Deposition Showed A New Side Of Jan
One of Michael's more wholesome moments was when he ed Jan at her deposition for wrongful termination against Dunder Mifflin. As Jan's boyfriend, Michael tried proving why Jan was in the right.
And while it was hard for Michael ing his girlfriend against his employer, he wasn't given the same respect from Jan. While at the deposition, Jan knew Michael was going to mess up so she stole Michael's journal as proof regarding their relationship. Michael felt betrayed because his journal was personal for him. This dark moment led to their fallout.