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13 "The Office" Moments So Embarrassing You Actually Feel Pain When You Watch Them

So funny, but so painful.

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13. When Michael sings to both Benihana waitresses because he can't tell them apart.

NBC

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.

12. When Jim accidentally reveals Pam's pregnancy at their rehearsal dinner.

NBC

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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11. When Michael tries to help the new guy onto the table.

NBC

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.

10. When Andy's dad shuts him down at the garden party.

NBC

The Episode: "Garden Party" (Season 8, Episode 4)

Why It Hurts To Watch: The whole reason Andy puts on the party is to impress his father, so it's all the more painful to watch him fail to sing "More Than Words" a few times before his dad completely takes over. Poor Andy.

9. When Michael brings in the building's property manager, Billy, to talk about disabilities.

NBC

The Episode: "The Injury" (Season 2, Episode 12)

Why It Hurts To Watch: The whole situation is vintage Michael Scott: Pulling the entire office into the conference room for a meeting that only serves to validate his own feelings. But when Michael says his Foreman-grilled foot injury makes him and Billy the same, it's almost too much to bear.

8. When Andy proposes to a very reluctant Angela.

NBC

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.

7. When Michael goes on a blind date.

NBC

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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6. When Toby gropes Pam's leg.

NBC

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.

5. When Michael proposes to Carol at the Diwali party.

NBC

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.

4. Literally anything that happens during Michael and Jan's dinner party.

NBC

The Episode: "Dinner Party" (Season 4, Episode 13)

Why It Hurts To Watch: Every moment of this disastrous dinner party — from the camera in the bedroom, to the aggressive use of the word "babe," to Jan dancing to Hunter's hit song "That One Night" — is cringe-inducing genius. The only thing keeping it from being the most cringeworthy episode ever is the fact that it's so damn funny (and that we're all hoping Jan and Michael will break up very soon).

3. When Michael prematurely announces Phyllis and Bob at their wedding.

NBC

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.

2. And when he forcibly gives a speech during the reception.

NBC

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.

1. When Michael faces the kids he promised college scholarships to many years ago.

NBC

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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