The Office: Top 15 Michael Scott Moments That Made Us Cringe Hard

Michael Scott Cringe moments from The Office
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The office USA is one of the most popular sitcoms of this generation and possibly the generations to come. If you have seen Office, You don't need an introduction to the regional manager of Dunder Mifflin, Michael Scott.

There were moments when he made us laugh and love him but the cringe moments surely outweigh the warm moments. Here is the list of 15 such cringe moments of Michael Scott.

1. Ruined a Perfect Date with Date Mike

The office employees are enjoying their happy hour when Jim and Pam decide to set up Michael with their friend. Everything is going smoothly and Michael is unknowingly charming his date until he finds out he is on a date. This is the moment when things start going downhill and Michael thinks of showing his charm.

He rushes to his car, pulls out a cap, Undoes a few buttons, and voila he is dating Mike. But this all goes wrong and he almost gets kicked out of the bar. One might think he ends up with his date, but Michael proves us all wrong and ditches her for the manager of that bar.

2. Pretended that he was not Michael Scott to get out of blind date

So our single regional manager forces his employees to set him up on a date. Not with any other girl but a beautiful, hot girl. Pam, being the sweetheart, Sets him up with her landlord.

Our ladies' man gets to the cafe and assumes a girl, completely different from the description, To be his blind date. When the real date arrives, He rudely refuses that he is not Michael Scott but gets caught. The date was really sweet but didn't fit Michael's expectations. 

3. Scott's Tots

This one is pitiful. Our favorite manager thought that he will be a millionaire by the time he is 40. Keeping this in mind he promised a class of third graders that he will pay their college fees if they get good enough grades.

The graduating class then invites Michael for a thank you program where they give heartwarming speeches and entertaining musical performances. Michael breaks their dream in a second and as compensation gives them laptop batteries. Not laptop but laptop batteries!

4. Promoted racial stereotypes unknowingly on diversity day

One person who is the epitome of racism, but he thinks he is not, has to be Michael Scott. This time our world's best boss decides to teach about diversity day to his employees. Let's make this clear how he is teaching them. He is using stereotypes to identify which race the other person belongs to. This ironic plan goes wrong when he impersonates in front of Kelly an Indian who goes too far and she slaps him hard across his face.

5. Kissed Oscar to prove he is not homophobic

Oscar Martinez is the gay character in the series but in the first season, he tries to hide it from everyone. Now Michael knows this, and being the excellent secret keeper that he is, he holds a meeting so that oscar can come out as gay in front of everyone.

Just to make the office environment a little more accepting to Oscar, he tries to hug him, oscar refuses, but he still does that. Now he takes this whole fiasco one step further and tries to kiss him to show that he is not Homophobic. This episode, without any doubt, ranks the episode with the most cringe in the entire series.

6. Proposed to Carol and later tried to kiss Pam

The Diwali episode was one of the failures in the love life of Michael Scott. Carol, Michael's girlfriend, shows up in a cheerleader's uniform because our main man told him it was a costume party. Not only this but he proceeds to propose to her in front of everyone, in haste.

But she rejects her proposal and he is left heartbroken. Here comes Pam Beasley to rescue and she tries to console Michael. But Michael takes her signals in the wrong way and he tries to kiss her. The cringe doesn't even end here as he shamelessly asks her for a ride home which she accepts but with one condition that he has to sit in the back.

7. Hosted the Dinner Party From Hell

Michael and Jan's relationship have to be one of the most toxic relationships in the history of sitcoms. The whole evening is spent throwing taunts and jabs at one another by Jan and Michael.

This all becomes too much for Michael when Jan throws a Dundie at the $200 plasma TV. The whole dinner party was a little too much to handle for Jim, Pam, Andy, Angela, Dwight, And for the audience too. 

8. Hosted The Dundies

Dundies were supposed to increase the morale of the employees but instead, they focused on their stereotypical qualities. The dundies started with a very poor hip-hop performance by our greatest showman complete with cue card mishaps.

The night gets racist when Michael hands the award "spicy curry" to Kelly because she is of Indian origin. Then he assumes that the lady sitting with Stanely is not his wife because she is white.

Phyllis and Angela get the award for those body parts that should remain unmentioned in an office workspace. If this all was not enough to make the audience cringe, Michale's stereotypical Asian impression certainly fulfilled that.

9. Grilled his foot on George Foreman Grill

"I like waking up to the smell of crackling bacon". This weird desire of Michael landed his foot in trouble when he accidentally burned his foot on the George Foreman grill which he kept right near his foot.

This made Michael think that he deserved the attention and everyone should care for him. When no one behaved as Michael wanted, he invited Billy merchant, the property manager who was in a wheelchair to talk about disabilities.

10. Transformed into Prison Mike

Michael would go to any limit to prove his point right. "The convict" episode confirms this point. When the office employees came to know that one of their co-workers served time in jail, they wanted to know all about his experience.

The description made Pam think that jail life is better than the life they have in the office. Michael gets enraged by this and demonstrates a whole other drama complete with a creepy character "prison mike" to show everyone that office life is much better than prison life.

11. Absurdity at Bob and Phyllis's wedding

Michael had this crazy habit of constantly involving himself in his employees' personal life. He constantly tried to highlight himself when Phyllis was walking down with her father.

After that, he untimely announced Phyllis and Bob as a couple, even before Bob said "I do". Michael was oblivious to the fact that he was ruining Phyllis' Special day with his Antiques.

12. Fake Fired Pam 

Our favorite regional manager of Dunder Mifflin Scranton would do anything to get a reaction. In this episode, he fake fires Pam to demonstrate to Ryan an experiment.

Not only did he fake fire Pam but in the later season, he fake fire Erin also. Michael didn't care about his employees' sentiments or how his actions might hurt his employees, he just wanted to be entertained.

13. Forced Meredith To Go Into Rehab

Everyone knows that Michael loved involving himself in his employees' business. During the office's Christmas party, Meredith lit her hair on fire and this convinced Michael that she had a drinking problem.

Michael, being the best boss and an amazing friend, thought to hold an intervention for her, to convince Meredith that she is an alcoholic. He didn't even stop there. Michael lied to Meredith and took her to a rehabilitation center and literally dragged her inside the center.

14. Dated Pam's Mom

Dating your employees' mom is as cringe as it sounds. Michael didn't agree with this point and went on to date Pam's mom. Poor Pam comes back from her honeymoon, all happy when she discovered that her boss is dating her mom.

The slap by Pam to Michael is totally justified after what he did. This behavior was not office-appropriate and made us cringe hard. The dating ends in a very rough way when Michael dumps Helene, Pam's mom, on her birthday and wins the award for the cringe boss.

15. Hit Meredith With His Car

This episode is a cringe-fest of not only Michael but Dwight also. So our photogenic regional manager is talking to the documentary crew while driving when he hits Meredith with his car.

Now Michael doesn't own up to the accident and tells everyone it wasn't really a big deal when it clearly was. Things just take a weird turn with the Dunder Mifflin employees visiting Meredith palmer in the hospital, Where Our Assistant to the Regional Manager, Dwight Schrute wants to unplug Meredith's life support to put her out of misery.

Typical Dwight! This episode was a win in some way as Meredith came to know she has rabies and also got her Fun run! Go, Meredith! 

Our favorite regional manager of Dunder Mifflin Scranton made The office worth watching because of his cringe moments. Go, Michael!

She/her. Feminist. Would love to open a dog shelter someday.

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