The Office – Michael’s 5 Cringiest Moments

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Pretty much all of The Office’s first seven seasons is one gigantic example of Michael and his cringe-inducing nature. He’s not a character known for his finesse, and his social awareness is zero, however, this is a list of Michael’s 5 cringiest moments in the show.


5. Michael’s Blind Date

Michael Blind Date

Whilst going through a romantic crisis, Michael asks the office if there’s anyone he can be set up with. Phyllis mentions a friend, to which Michael asks if she can fit in a sailboat, in a not-so-subtle way of asking her weight. Pam then takes pity on him and sets him up with her landlord Margaret, which in true Michael fashion, goes terribly. He arrives at the coffee shop, and upon seeing his blind date pretends not to be Michael, until the barista hands him his coffee, blowing his cover in the process. What follows is a conversation that could be used as an example of what NOT to do on a first date.

4. Date Mike

michael's 5 cringiest moments
Steve Carell as Date Mike

Another cringe moment, another romantic involvement. The gang go out to a local bar, and for some reason, Pam once again invites a friend with the intention of setting Michael up with her. Before Michael realises it’s a date, he’s actually doing relatively well, but as soon Jim clues him in, Michael brings out ‘Date Mike’, a flat cap wearing, obnoxious parody of himself. Safe to say chaos ensues.


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3. Oscar’s Kiss

Steve Carell and Oscar Nunez Go Off Script

The first unscripted moment in Michael’s 5 cringiest moments, Oscar is unfortunately outted as being gay by Michael. In his own special way, Michael thinks he’s helping, when in a bid to show he’s not homophobic, he has Oscar stand in front of everyone for a hug. Awkwardness and second-hand embarrassment aplenty, what was not in the script was for Steve Carell to actually kiss Oscar Nunez. The rest of the cast’s reactions are all real, as they weren’t aware of the improv at the time.

2. Scott’s Tots


I’m sure you expected this to be number one, and in fairness, this is a big one. Having promised years prior to pay the tuition fees for a class full of children, Michael realises the enormity and cost of his promise when the time comes to pay. An entire episode of him trying to find ways out of facing the music, culminates in him breaking the news to the students, after they’ve lavished him with praise and thanks. He does offer them laptop batteries though!

Also read: Best Moments From The Office Listed

1. Diversity Day

Diversity Day in The Office

Number one on Michael’s 5 cringiest moments and it’s not a good look for him either. Thanks to a complaint to HR after a particularly poor impersonation of a famous Chris Rock stand-up routine by Michael no-less, the office has to have a discussion on diversity and inclusiveness. This devolves into Michael taking over the seminar, and his idea for diversity training is to give a different race or religion to be, and asks them to portray in the most stereotypical and racist way possible.


Honourable Mentions

The entire show is one big honourable mention to Michael’s cringe, but there’s a few more standouts that didn’t make the list. The famous dinner party episode where he ends up in a huge argument with Jan, having tried to tap up his guests for an investment being one, his tantrum at not being able to play Santa for the office christmas party being another, as well as many, MANY more.

That’s my choices for Michael’s 5 cringiest moments. What have I missed and what would you have added?

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Written by Luke Addison

Articles Published: 437

Luke Addison is the Lead Video Game Critic and Gaming Editor. As likely to be caught listening to noughties rock as he is watching the latest blockbuster cinema release, Luke is the quintessential millennial wistfully wishing after a forgotten era of entertainment. Also a diehard Chelsea fan, for his sins.

Twitter: @callmeafilmnerd