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15 Moments from ‘The Office’ that Always Make You Cringe

Published on October 5th, 2017 | Updated on October 5th, 2017 | By FanFest

15. Jim Announces Pam is Pregnant

The Episode: "Niagara, Part 1" (Season 6, Episode 4)Why It Hurts To Watch: There's a big to-do about how Pam's very conservative grandmother is the only one who doesn't know about the pregnancy, so there's that. Then, Michael tries to mitigate the situation by saying that Jim and Pam "made a mistake." Plus, Jim is usually so smooth, so it's tough to watch him flounder.

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The Episode: “Niagara, Part 1” (Season 6, Episode 4)

Cringeworthy Recap: Jim and Pam had made a huge deal to everyone in the office not to say anything about Pam being pregnant because of her very traditional and conservative grandmother. S0, when Jim, who is usually so smooth, is the one to spill the beans it’s hard to watch him flop around mid-toast and poorly cover his tracks. Plus, add in Michael intervening saying that the two had “made a mistake” and you’ve got a whole bunch of awkward.

14. Michael Can’t Tell Which Girl is His Date

The Episode: "A Benihana Christmas" (Season 3, Episode 10)Why It Hurts To Watch: The whole situation is awkward enough, but the moment of panic of Michael's face just tops the whole thing off. And when he marks her later? Oof. Plus, they're singing "Your Body Is a Wonderland," which cranks the embarrassment factor to 11.

Cringe Meter

The Episode: “A Benihana Christmas” (Season 3, Episode 10)

Cringeworthy Recap: First of all, the fact that they’re singing “Your Body Is a Wonderland” only amped up the awkwardness that was this entire episode, but the look on Michael’s face when he realizes that he can’t remember which Benihana waitress was his date is pure cringe. Not to mention he later marks her, so there’s that.

13. Date Mike

Cringe Meter

The Episode: “Happy Hour” (Season 6, Episode 21)

Cringeworthy Recap: Date Mike is cringey on his own, but it really is Michael choosing to become Date Mike that is even worse. While out with Pam, Jim, and Pam’s friend, Michael is totally charming and his it off really well with Julie, that is until he learns that he’s actually on a date with her. Then, in the blink of an eye, he transforms into the “chick magnet” that is Date Mike and everything barrels downhill shortly after.

12. Diversity Day

Image result for the office diversity day

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The Episode: “Diversity Day” (Season 1, Episode 2)

Cringeworthy Recap: Diversity Day was going to be a disaster from the start because if there’s one person who should not be teaching messages on racial tolerance it’s Michael Scott. Watching everyone try to scoot around giving clues to the cards on people’s heads was bad enough, but then when Michael takes it too far, Kelly slaps him in front of everyone and it is so uncomfortable to watch.

11. Andy proposes to Angela

The Episode: "Goodbye, Toby" (Season 4, Episode 18/19)Why It Hurts To Watch: Andy's clumsy intro is awkward enough, but then Angela replies with a defeated "OK" that Andy makes her repeat into the microphone. As if all of that wasn't painful enough, we see just how sad Jim and Pam are that their moment was hijacked.

The Episode: “Goodbye, Toby” (Season 4, Episode 18/19)

Cringeworthy Recap: Andy’s harmless, but he sure does not know how to read a situation. Not only is his speech a rough start, but then he has to run off stage to get to Anglea and then makes her repeat her solemn “OK” into the microphone, all while Jim stares on in horror because he was planning on proposing to Pam that night.

10. When Michael Spanked the Intern

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The Episode: “Nepotism” (Season 7, Episode 1)

Cringeworthy Recap: Michael spanks his adult nephew in front of everyone in the office – need I say more?

9. Toby Touches Pam’s Leg

The Episode: "Night Out" (Season 4, Episode 11)Why It Hurts To Watch: Toby's obsession with Pam is always a bit sad and awkward, but everything here — the creepy finger caress, the announcement about Costa Rica, and the run out the door and over the fence — is the worst thing he's ever done.

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The Episode: “Night Out” (Season 4, Episode 11)

Cringeworthy Recap: It was always kind of sad and weird to watch Toby’s attraction to Pam over the years, but when he awkwardly touched her leg, then announced he was moving to Costa Rica, and then ran and jumped over the fence, he really Out-Toby’d Toby.

8.Michael’s Blind Date

The Episode: "Chair Model" (Season 4, Episode 10)Why It Hurts To Watch: Michael is often oblivious, but he's very rarely just straight-up mean. Here, though, he does nothing to hide his disappointment over the attractiveness of his blind date, and it makes the entire thing one of the most cringeworthy scenes in the entire show.

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The Episode: “Chair Model” (Season 4, Episode 10)

Why It Hurts To Watch: This almost would have been better if he had just brought out Date Mike because there was nothing funny about this scene. It’s actually one of the few times that Michael is just straight up mean. He doesn’t hide his distaste or disappointment over what his blind date looks like and pretends to not be Michael even though the barista is trying to give him his drink. The whole scene is just horrible horrible horrible.

 7.Michael Kisses Oscar

Image result for michael kisses oscar gif

Cringe Meter:

The Episode: “Gay Witch Hunt” (Season 3, Episode 1)

Cringeworthy Recap: To prove to everyone that he is not homophobic, Michael decides to prove his openness by spontaneously kissing Oscar in the conference room. The worst part isn’t the kiss though, it’s the slow burn leading up to the kiss.

6. Michael’s Speech at Phyllis’ Wedding

The Episode: "Phyllis' Wedding" (Season 3, Episode 15)Why It Hurts To Watch: Yes, this episode is so painful it has two moments on the list. Phyllis is such a sweet character, you never want anything bad to happen to her, so when Michael gives the most embarrassing speech you could think of at her reception, her face just makes you so, so sad.

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The Episode: “Phyllis’ Wedding” (Season 3, Episode 15)

Cringeworthy Recap: Phyllis’ wedding was filled with so many awkward moments at the hands of Michael that it was almost unbearable. One moment that tops the list is his embarrassing speech in which he tells everyone that her high school nickname was “Easy Rider”. Poor Phyllis.

5.  Phyllis and Bobs Wedding Announcement

The Episode: "Phyllis' Wedding" (Season 3, Episode 15)Why It Hurts To Watch: Generally, Michael's embarrassing moments are in the relative privacy of the Dunder-Mifflin office. That's not the case here, where he very loudly interrupts Phyllis's wedding ceremony, and not for the first time.

Cringe Meter:

The Episode: “Phyllis’ Wedding” (Season 3, Episode 15)

Cringeworthy Recap: Just the public nature of this moment alone is extremely cringey, and then the fact that he waits around until the appropriate time to do it all over again is even worse.

4. Michael Proposes to Carol 

The Episode: "Diwali" (Season 3, Episode 6)Why It Hurts To Watch: You know that Michael's heart is in the right place, but it's really just his desperation speaking. Oh, and the fact that Carol is in a cheerleader outfit because Michael told her that Diwali is "like Indian Halloween" makes it all even worse.

Cringe Meter:

The Episode: “Diwali” (Season 3, Episode 6)

Why It Hurts To Watch: It’s important to remember that Carol is in a cheerleader outfit because Michael had told her that Diwali is basically an “Indian Halloween”. Michael was just proposing out of desperation and even though we all knew that, watching Carol’s rejection in front of everyone was so awkward and sad.

3.  Tony and the Table

The Episode: "The Merger" (Season 3, Episode 8)Why It Hurts To Watch: It's clear from the moment the Stamford employees show up that Tony doesn't want any part of Michael's crap, so when Michael forces him up on the table, you can just feel Tony getting ready to quit.

Cringe Meter:

The Episode: “The Merger” (Season 3, Episode 8)

Cringeworthy Recap: I still can’t watch this scene without having to look away. It was a perfect example of Michael’s ineptness and inability to read a situation.

2. The Entire Dinner Party Episode

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The Episode: “Dinner Party” (Season 4, Episode 13)

Cringeworthy Recap: There were just too many classic moments from this episode to only pick one photo. The entire dinner party is a complete disaster filled with cringey moments and hilarity, making it one of the best episodes of the series. From Michael’s plasma TV to Jans inability to serve dinner to Dwight and his old babysitter crashing, “Dinner Party” is the some of the most cringe-worthy yet enjoyable material of the show.

1. Scotts Tots

The Episode: "Scott's Tots" (Season 6, Episode 12)Why It Hurts To Watch: There's a slow build throughout this episode as you gradually learn the details of the "horrible thing" Michael did. When you see just how overjoyed the kids are that Michael is going to pay for their college education ("Hey Michael Scott, whatcha gonna do? Whatcha gonna do, make our dreams come true!"), it makes Michael's truth bomb hurt. So much.

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The Episode: “Scott’s Tots” (Season 6, Episode 12)

Cringeworthy Recap: 

When you think of the worst thing that Michael Scott ever did on The Office, chances are you go straight to Scott’s Tots, the group of kids that he promised he would pay all of their college education for once they graduated high school. Well, Michael can barely afford a condo in Scranton so it was immediately clear that he was going to have to tell these kids that the free education they worked so hard for was nowhere in sight. Instead, he got them some laptop batteries. It. Is. The. Worst. It’s peak Michael Scott and will always be the ultimate cringe moment.



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