In the sixth season of The Office, Michael unexpectedly met a woman named Donna Newton and became infatuated with her. After going to Sid & Dexter for an office happy hour, the two met after Donna scolded him for his behavior in her bar. But after talking, the two began flirting and made a meeting for Donna to visit Dunder Mifflin to look at printers.
What started with a printer ended in a relationship. Soon after that fateful night, Donna and Michael began dating, but it wasn't the relationship everyone thought it was going to be...
Good Together: They Were Both Outgoing And Fun
Michael is a kid at heart. As a man in his forties, he's boisterous and outgoing and would rather be on an adventure than doing paperwork. Likewise, with Donna as a manager of an adult arcade of sorts, she too has a playful side. Viewers didn't see too much of their life together but they can imagine them having drinks at the arcade, going bowling, or skiing in the Poconos.
The Worst: She Was Married!
Here's the elephant in the room: Donna Newton was a married woman. As a single man who believes in monogamy (as fans have seen with his other relationships), it was extremely out of character for Michael to be interested in a married woman.
He was a man who wanted a wife and kids. How was he going to achieve that with a woman who already had a husband? After Michael found out Donna was married, he should have ended the relationship immediately.
Good Together: She Was Equally Interested In Him
Michael Scott is incredibly childish, but he's a handsome man with a semi-good head on his shoulders. The problem with Michael is that he's typically more interested in the relationship than his girlfriends are. He pushed Carol Stills too far with their holiday card and she broke up with him right before Christmas. He was always more interested in Jan than she was in him. And as for Holly, Michael wanted it to work but knew it would be one-sided. When it comes to Donna, she was just as interested in Michael as he was in her. This was a first for him.
The Worst: Their Relationship Proved How Desperate Michael Was
As soon as Michael found out that Donna was married, he should have bolted. By willingly entering an affair, it proves how desperate Michael was. He wanted to be with a woman who wanted to be with him, no matter whose feelings got hurt.
During the Donna era, he had nothing outside of work going for him. His friends and his "family" were inside the office. Having someone to curl up to outside of the office was all Michael wanted. Even though Donna was a taken woman, she still filled that void for a short time.
Good Together: They Were Both Managers
With Michael and Donna being managers of their chosen field, they had things in common and something to talk about. They probably confided in each other over work issues or how to get employees to listen to them or like them. Michael probably made working at Dunder Mifflin seem magical to Donna even though it was your standard run-of-the-mill paper company. Nevertheless, having commonalities in a relationship is important.
The Worst: They Showed No Remorse
After Michael found out that Donna was married, he showed no remorse for his actions. He was devastated that a woman he cared for so much was already in a committed relationship but never once did he think about the third party involved, Donna's husband, Shane.
To show Michael was he was doing to another man, Andy took Michael to Shane's baseball game. Shane coached a local team, which was the perfect setting for Michael to see what he was like as a person. At the game and after, Michael's feelings about the situation did not change one iota.
Good Together: She Got Him Outside Of The Office
Before Holly, Michael's entire life was Dunder Mifflin. The only thing he did for himself outside of the workday was attending improv classes. Michael loved to act and wrote screenplays when he wasn't working. But that can only take up so much of Michael's time.
When he started dating Donna, she got him out of his shell and doing things. They were constantly going on mini getaways as a couple, which opened Michael's eyes to different parts of Scranton. He later realized she only took him on getaways because she didn't want her husband catching them —but it was still time away from the office.
The Worst: Was It Only Sexual?
One has to ask themselves if the relationship between Michael and Donna was from the heart or if it was only physical. Besides being managers, what did the two of them have in common? And can Donna really be trusted if she omitted the fact that she was married? It makes you wonder what else she lied about to poor Michael.
Good Together: She Didn't Mind The Unique Characters At Dunder Mifflin
Fans have to give Donna credit for visiting Dunder Mifflin as often as she did. She stopped by to talk to Michael when she was "interested" in buying a printer and she came by to yell at him when he had Dwight follow her.
Michael and Donna weren't together for a long period of time but she already had run-ins with Jim, Pam, and Dwight, and seemed to leave unscathed. Not too many women could say the same.
The Worst: His Friends Lost Respect For Him
Michael is nothing without his buddies at Dunder Mifflin. Pam, Jim, Dwight, and co. were his friends and closest confidants. If he didn't have them, who did he have? For his own sake, he needed to date a woman that his co-workers and friends liked. He couldn't get himself into another situation where his friends didn't want to come over for a dinner party in fear of his relationship.
When everyone found out Michael was still seeing Donna even though she was married, they all lost respect for him. The only thing he could possibly do to save his friendships was to leave her.