So funny, but so painful.
When Michael sings to both Benihana waitresses because he can't tell them apart.
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.
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When Jim accidentally reveals Pam's pregnancy at their rehearsal dinner.
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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When Michael tries to help the new guy onto 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.
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When Andy's dad shuts him down at the garden party.
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.
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