The Most Cringe-Worthy Michael Scott Moments Ever!

A man pointing while wearing a bandana
Credit: NBC

If we were completely honest, there are too many cringe-worthy Michael Scott moments to make the cut. And even writing this article is both painful and hilarious at the same time. Here are our favorite Michael Scott moments that make us feel both violently sick and make our toes curl…

Diversity Day

A man wearing a post-it note on his head while holding a cup in his hand
Credit: NBC

One of the first glimpses into how incredibly awkward Michael can be. Of course, Michael’s ideas get away with him. He doesn’t realize he is the reason why a special consultant has to teach the office about diversity, as he offends everyone with his ‘Chris Rock’ routine. It would be hard to count the number of times offensive comments are made by Michael, with the cringiest moment occuring when he speaks to Kelly in an accent. Only the second episode of the whole show, yet one of the most moments of the entire series.

Dinner Party

A man and woman arguing as he points at the tv
Credit: NBC

Dinner Party remains one of the most popular episodes according to fans, but it isn’t short of some of the most cringy moments of the whole show. This episode is where we really get to see the toxic, complicated relationship between Michael and Jan. From the argument about the ‘plasma tv’ to the conversation about Michael’s vasectomy, everyone single person is bound to watch this monstrosity through their fingers. Even the cast found it incredibly cringy – just watch the bloopers from this episode as you will see the reactions of having to film these scenes! Incredible!

Gay Witch Hunt

Two men kissing very awkwardly
Credit: NBC

This scene is more than likely imprinted in your brain. What makes this scene so amazing is the reactions of all the cast, as no one knew that Michael was going to plant a kiss on Oscar. As Michael attempts to prove how comfortable he is that Oscar is gay, he instead manages to make the whole office feel like they want the floor to swallow them up. We really don’t know how they didn’t break character with this – one of the funniest and embarrassing moments ever!


A man claiming that he couldn't hear what someone said
Credit: NBC

Witnessing Michael’s love life has too many cringe-worthy moments to count on our fingers and toes – and this one is up there with some of the worst! The relationship with Carol is short-lived (played by Carrell’s real-life wife), and we start to understand why it’s life expectancy was so small. Michael proposes to Carol after only 9 dates, and what makes this moment even worse is that he refuses to hear what she has to say. We can’t watch…

Classy Christmas

A woman holding a toy story doll up looking confused
Credit: NBC

Another Michael Scott moment which makes us wonder how he ever got a woman to fall in love with him, never mind Holly herself. As Holly returns to the Scranton branch, Michael attempts to do anything in his power to win her back, especially as she is dating AJ. Michael’s ‘genius’ idea backfires massively as he decides to deface Holly’s Woody figure, something she cherishes. What makes the whole situation worse is the fact that Michael tries to squirm his way out of it rather than initially holding his hands up. At least it works out for them in the end!

Phyllis’ Wedding

A man making a speech at someone's wedding
Credit: NBC

Phyllis is getting married. And I am in the wedding party. She has asked me to push her father’s wheelchair down the aisle. So, basically, I am co-giving away the bride. Since I pay her salary it is like I’m paying for the wedding. Which I’m happy to do. It’s a big day for Phyllis. But it’s an even bigger day for me. Employer of the bride.

Double Date

A man and woman having a conversation while out for dinner
Credit: NBC

This pairing alone started off extremely embarrassing (we all can’t forget the scene where Pam finds out Michael is dating her mother). The awkwardness of how this relationship starts is outdone by how the relationship ends. While on the double date, Michael realizes how incompatible he and Helene are. As Michael works out how old Helene actually is, that’s when things truly turn south, with Michael suggesting they participate in a triathlon, where she responds that she has done one when she was younger. Very cringe-worthy, yet extremely humorous!

Chair Model

A man and woman chatting
Credit: NBC

Possibly one of the cruelest Michael Scott scenes, while still being massively cringe-worthy at the same time. Pam introduces Michael to her landlady on a blind date as he recently breaks up with Jan. As her physical appearance doesn’t match what Michael hopes for, he instantly starts being rude on the date. Watching Michael struggle to use any form of social skill is an unpleasant feeling.

If you are a big Michael Scott fan, then you need this!

Benihana Christmas

Credit: NBC

One of our favorite Christmas episodes, full of Michael Scott moments that are so shameful that it’s enough to put you off the holiday season altogether! With one of the most awkward scenes ever where Michael can’t distinguish who is who between the two waitresses so decides to mark one with a black marker. And not forgetting his duet with Andy. Absolute comedy gold from Michael, yet we can’t help but grimace throughout the hour-long special!

Scott’s Tots

A man crying while everyone stares at him
Credit: NBC

How could we forget the world’s most cringe-worthy episode of any show in the entire universe ever! From start to finish the episode is unbearable to watch as we see Michael try and crawl out of the numerous mistakes he has made. When we think about it, it’s actually sad to see a man offer kids the opportunity of a lifetime because he thinks he will be rich in time, but sadly it just isn’t the case. And the song. Boy, how can we forget the routine that actually makes you want to turn the episode off. We can’t bear it, yet we can’t keep our eyes off the screen. The Office truly outdid themselves with this episode. Bravo!

And we could have included so many more moments. From Michael fake firing Pam in the very first episode to Michael and Dwight helping Tony on the table. If anything, it would have been easier for us to count the times Michael Scott did embarrass us to our very core. But we still love him so much. And if you don’t pull the face above for the entirety of The Office, then you are watching it wrong!

Want to know what department we think you would be perfect in? Take this quiz to see where you are best suited at Dunder Mifflin!