Moments From The Office That Made Us Feel Bad For Michael Scott

List Rules
Vote up the moments that made you wish you could give Michael a hug

Michael Scott is by no means an easy person to work with, but he has a big heart and a tendency to let people walk all over him. Despite all the horrible, cringe-worthy moments that Michael puts us through during the show, there are nearly as many times where we can't help but feel sorry for the guy. Over the course of the series, Michael slowly learns how to laugh at himself, how to stand up for himself, and how to think about others before himself — but that growth is made possible by tough experiences that audiences go through with him.

Redditors on the popular The Office subreddit came together to chronicle some of the moments from the sitcom that made them feel for Michael Scott. Take a look at the episodes and stories they picked an vote up the ones that made you pity the irrepressible branch manager. 

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  • 1
    52 VOTES

    Michael's Terrible Halloween (S2E5)

    Michael's Terrible Halloween (S2E5)
    Photo: NBCUniversal / Peacock

    From Redditor u/AUMiklo:

    When he's sitting by himself on halloween night after having to fire Devin. He agonized over it and while the cameras make it appear he is just worried about how people perceive him he does care about his coworkers. As the branch manager, he's the classic middleman who often gets put in a no-win position.

    52 votes
  • 2
    47 VOTES

    Michael And Pam Learn Holly Has A New Boyfriend (S5E17)

    Michael And Pam Learn Holly Has A New Boyfriend (S5E17)
    Photo: NBCUniversal / Peacock

    From Redditor u/Avokei:

    When he goes with Pam to see Holly and he finds out she has a boyfriend.

    47 votes
  • 3
    73 VOTES

    Michael's TV Appearance (S2E18)

    Michael's TV Appearance (S2E18)
    Photo: NBCUniversal / Peacock

    From Redditor u/lumberjake1:

    I Want To Be Married And Have A Hundred Kids So I Can Have A Hundred Friends, And No One Can Say No To Being My Friend.

    Michael goes through the trouble to find a video tape of an appearance he made on a children's show years ago called Fundle Bundle. The clip shows feline puppet character Edward R. Meow asking young Michael what he wants to be when he grows up, and Michael's response is so depressing it leaves even his puppet interviewer dumbfounded.

    73 votes
  • 4
    66 VOTES

    The Deposition (S4E12)

    The Deposition (S4E12)
    Photo: NBCUniversal / Peacock

    From Redditor u/wjglenn

    When he finds out that Jan planned to reveal his diary all along and also that he was never a real candidate for the corporate job.

    66 votes
  • 5
    31 VOTES

    Michael Decides To Wait For Holly (S5E28)

    Michael Decides To Wait For Holly (S5E28)
    Photo: NBCUniversal / Peacock

    From Redditor u/-leeson:

    When they’re at the company picnic and he plans to try and win Holly back, but then says, 'I didn't find the perfect moment, because I think today was about just having today. And I think we are one of those couples with a long story when people ask how we found each other. I will see her every now and then, and maybe one year, she'll be with somebody, and the next year, I'll be with somebody and it's gonna take a long time. And then it's perfect. I'm in no rush.'

    31 votes
  • 6
    46 VOTES

    Michael Hides His Second Job (S4E7)

    Michael Hides His Second Job (S4E7)
    Photo: NBCUniversal / Peacock

    From Redditor u/viewfrom360:

    When he gets a second job as a telemarketer where he feels he needs to lie to Jan about going to improv, because he's insecure about not having enough money, but then he's not even good at the job and envies Vikram who gets the most sales. Even after he insults Vikram by saying egotistical and insensitive comments about how he'd be in a career above Vikram's if he lived in his home country, Vikram feels bad for him at the end of the night and gives him some encouragement.

    46 votes