The Office: 10 Worst Things Michael Scott Ever Did

It's safe to say that Michael and relationships didn't blend too well. His way with women was less like a smooth ride and more a car wreck. He constantly overstepped boundaries and struggled to take responsibility for anything he did wrong. This was abundantly clear in his toxic relationship with Jan Levinson.

At first, these two seemed like a great opposites attract moment, but that soon faded. Michael was way too eager initially, especially as Jan insisted they were not a thing and that their drunken kiss was a mistake. His insistence somehow paid off, as they eventually did become something, but Michael soon learned that her coldness and mistreatment wasn't what he wanted.

However, after breaking up with her, she revealed that she'd had breast augmentation surgery, and against his better judgement, he ran right back to her. It all culminated with the utterly horrifying episode "The Dinner Party", in which the duo hosted an evening at their home and let all the issues in their relationship slip out.

While Jan certainly didn't come out of this looking great, Michael had strong-armed this relationship into being and then realised that he never even wanted it. It wasn't all his fault, but his behaviour fanned the flames that burned them down.