Almost all of The Office’s first seven seasons are a gigantic example of Michael and his cringe-worthy nature. He’s not a character known for his shrewdness and his social conscience sucks, however, here’s a list of Michael’s 5 scariest moments on the show.
5. Michael’s Blind Date
While going through a love crisis, Michael asks the office if there is anyone he can be set up with. Phyllis mentions a friend, whom 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 his landlady Margaret, which, in Michael’s fashion, is going terribly well. He arrives at the cafe and, upon seeing his blind date, pretends not to be Michael, until the barista hands him his coffee, blowing his blanket in the process. The following is a conversation that could be used as an example of what NOT to do on a first date.
4. Date with Mike
Another cringe moment, another love affair. The gang go to a local bar, and for some reason Pam invites a friend over again with the intention of setting up Michael with her. Before Michael realizes it’s a date, he does relatively well, but as soon as Jim gives him hints, Michael pulls out “Date Mike”, a flat cap wearing a parody hateful of himself. Safe to say chaos ensues.
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3. Oscar’s Kiss
The first unscripted moment of Michael’s 5 Scariest Moments, Oscar is sadly introduced as being gay by Michael. In his own way, Michael thinks he’s helping, when in an effort to show that he’s not homophobic, he asks Oscar to stand in front of everyone for a hug. Awkwardness and second-hand embarrassment aplenty, what wasn’t in the script was Steve Carell actually kissing Oscar Nunez. The other cast reactions are all real, as they were unaware of the improv at the time.
2. Scott’s toddlers
I’m sure you expected it to be number one, and in all honesty, it’s a big deal. Having promised years before to pay the tuition for a class full of children, Michael realizes the enormity and cost of his promise when it comes time to pay. An entire episode of him trying to find ways not to face the music, culminates in him breaking the news to the students, after they lavish it with praise and thanks. However, he offers them laptop batteries!
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1. Diversity Day
Number one on Michael’s 5 Scariest Moments and it’s not a good look for him either. Thanks to a complaint to HR after a particularly poor imitation of a famous Chris Rock stand-up routine by Michael no-less, the office needs to have a discussion about diversity and inclusion. It goes back to Michael taking over the seminar, and his idea of diversity training is to give away a different race or religion, and ask them to represent in the most stereotypical and racist way possible.
Honorable mentions
The whole show is a big honorable mention to Michael’s grimace, but there are a few other standouts that don’t make the list. The famous dinner episode where he gets into a huge argument with Jan, after he tries to recruit his guests for an investment by being one, his anger at not being able to play Santa for the office Christmas party by being one other, as well as many, many more.
This is my pick for Michael’s 5 Scariest Moments. What did I miss and what would you have added?
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