Michael Scott might think he’s the world’s best boss and a total ladies’ man, but really, he’s racist, sexist, and super selfish. And for every moment he does something nice for one of his employees, there are a zillion more in which he’s incredibly cringey.
Until settling down with Holly Flax, Michael Scott’s love life involved a series of destructive and disastrous relationships, like the time he broke every workplace rule by dating Helene Beesly, Pam’s mom. After meeting at Jim and Pam’s wedding, Michael and Helene hit it off, much to Pam’s horror. Eventually, Jim and Pam are forced on a double date with Michael and Helene. When Pam sees how happy her mom is with Michael, she warms up to the idea that her boss might one day be part of the family. Unfortunately, the birthday party is full of twists and turns, and while giving Helene a series of elaborate gifts, Michael finds out his girlfriend’s age, and suddenly realizes she’s a lot older than him.
As a result, he begins looking for a way out of the relationship, right there in the restaurant, on her birthday. Jim and Pam watch, mortified and shocked, as Michael lists all the reasons he should split up with Helene, such as the fact that he wants to have kids, visit Italy, and skydive, all stuff he probably should’ve discussed with his girlfriend before professing his undying love to her. Obviously, the whole date is incredibly painful to watch, but at least Michael gets his comeuppance when Pam slaps him across the face.
Michael Scott and Ryan Howard have always had a weird relationship. Michael wants to be Ryan’s mentor, his best friend, and occasionally, his lover. Unfortunately, this obsessive friendship only goes one way, so Ryan manipulates his boss. Case in point, when Ryan brings Michael to his business school so he can do a Q&A.
Michael can’t wait to impart his wisdom to the next generation. Sadly, it’s all a set-up. Ryan has no respect for his manager or the paper business, and he knows the class will eat Michael alive. Of course, Michael does a pretty good job of sabotaging himself, by walking into the classroom accompanied by his own theme song. Plus, Michael is a big believer in visual aids, and one of his teaching methods involves hitting a student in the head with a candy bar. The most awkward moment comes when Michael explains the basics of business to these MBA students, lecturing that,
But once the students start asking questions, it becomes painfully obvious that Michael is in way over his head. The final twist of the cringey knife comes when he discovers that Ryan has betrayed him. It’s a humiliating experience, but at least Michael gets the last laugh by forcing Ryan to work alongside his least favorite person in the office, his own girlfriend, Kelly Kapoor.
Watch the full video to see more Michael Scott moments that made Office fans cringe.
Pam’s mom | 0:00
Business lecture | 1:28
Booze cruise dance | 2:52
Hosting the Dundies | 4:08
Meet Date Mike | 5:01
The rebound | 6:21
New employee welcome | 7:30
Ruining Phyllis’ wedding | 8:48
Scott’s Tots | 10:05
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