The 8 absolute cringiest Michael Scott quotes in ‘The Office’ history

As the vast and fervent fandom of The Office knows, March 15 is notable for two, and only two, birthdays: those of Michael Scott and Eva Longoria, a fun fact Scott points out in the Season 2 episode “Michael’s Birthday.”

His follow-up about having an icebreaker if he ever meets Longoria’s Desperate Housewives co-star is … just so inherently Michael. 

The episode is a great reminder of just how cringe-worthy Michael can get. He insists the entire office celebrate his birthday as opposed to worrying about accountant Kevin, who may or may not have skin cancer.

But isn’t this Michael’s primary job, to make us totally cringe while he barely dabbles in managing the Scranton branch of the Dunder Mifflin Paper Company?

Steve Carell brought the character’s most frustrating aspects to life as vividly as he did the heartwarming ones. (I don’t think I’ve been as physically uneasy as I was watching Michael interrupt Phyllis and Bob’s nuptials to announce them as a married couple poor Bob gets a chance to say “I do.”)

And so, as my gift to Michael Scott on his 55th birthday — and to all of us except Eva Longoria/Teri Hatcher, on any given day — here are the Michael Scott moments that would truly embarrass any living human … anyone but Michael Scott, that is. 

1. “Diversity Day” — Season 1, Episode 2

When Michael took over for corporate liaison Mr. Brown to conduct diversity training, his method included sticking an ethnic label on every employee’s head, making them act out stereotypes, and then saying out loud that he didn’t have anyone be an Arab because it would be “too explosive.”

Literally no one except his right hand man Dwight Schrute seems enthusiastic, and Michael ends up getting slapped by Kelly Kapoor (Mindy Kaling) for badly imitating an Indian accent.

2. “Sexual Harassment” — Season 2, Episode 2 

Michael spends the episode getting schooled by corporate on appropriate workplace behavior. Despite this, when someone makes fun of how his employee Phyllis looks, he attempts to make her feel better by giving her a quick kiss on the cheek and telling her he’s now worried about getting a boner. 

You don’t need to see her expression to know that she is not amused. 

3. “The Injury” — Season 2, Episode 12

After barely injuring his foot on a George Foreman grill in this iconic episode, Michael uses crutches to walk around at work and boldly refers to himself as disabled. When his employees make fun of him, he asks if any of them know what it’s like to face disability. 

Phyllis says she had scoliosis as a young girl, but apparently that’s not a satisfactory answer. 

4. “A Benihana Christmas” — Season 3, Episode 10

Michael’s girlfriend/real-estate agent Carol dumps him for being too extra, which, understandable. In his tearful state, he doesn’t hesitate to call her his “ho.” The “you” he’s referring to here is … himself. 

Later in the episode, he is unable to tell which of two Asian waitresses from Benihana is his date to the office Christmas party. 

Classic dick moves all around. 

5. “Phyllis’s Wedding” — Season 3, Episode 16

Ah, yes, this is my favorite episode to watch when I want to recoil with discomfort. 

It’s Phyllis’s wedding and Michael has taken it upon himself to steal the show. He’s supposed to push her father’s wheelchair down the aisle, but midway, the dad decides to walk by himself. 

Clearly shaken at his limelight being stolen, Michael proceeds to slow walk to the altar as everyone looks on. The horror. 

6. “Chair Model” — Season 4, Episode 14

Look who’s back in the dating game! Michael, upon breaking up with girlfriend Jan, asks his employees to abandon everything in the middle of a work day and set him up on a date. 

Phyllis has someone great in mind, but he crushes his chances when the first question he asks is about her weight. 

On the plus side, Kevin tricks him into calling a Wendy’s by making him assume Wendy is a woman.  

6. “Double Date” — Season 6, Episode 9

Michael breaks up with Helene, his former secretary’s Pam’s mom, on her birthday (!) — as a cake-eating Jim and Pam observe in shock (!!) — for being “too old” (!!!). 

It’s horrifying because he dated Pam’s mom when Pam explicitly told him not to, and now, when Pam is finally okay with it, Michael ends things at literally the worst possible moment using the worst possible words. 

7. “Scott’s Tots” — Season 6, Episode 12

This is an episode I’m sure most fans of The Office tend to skip during their rewatch. It’s entirely cringe-inducing, and not in a funny way. 

Michael has to break the news to some high-school graduating kids that he can’t, as promised 10 years earlier, actually sponsor their college tuition. They’ve just gotta deal with the fact that they can’t go to college now. As compensation, he offers them all laptop chargers. 

Can I just say, his own intuition coulda and shoulda guided him better. 

8. “Body Language” — Season 6, Episode 23

Michael is excited to welcome his crush and potential client Donna, a bar manager, to the office. He spends the entire episode trying to kiss her and loops everyone at work — including Jim and Pam, who are doing the sales pitch for her — into very reluctantly giving him advice. 

When she walks in, he comes up with quite the greeting. Yikes. 

So, yeah. Happy birthday, Michael — it’s a big one.