The Office: 12 Most Cringeworthy Scenes

4. Michael Kisses Oscar

Scotts Tots The Office Michael Scott
NBC

As seems to be a theme with the cringeworthy moments on this list, this one also starts with Michael Scott. In this instance, it was when he used a homophobic slur against Oscar for enjoying Shakespeare in Love more than Die Hard.

While trying to make things better, Michael ended up making Oscar feel even more uncomfortable, alienated, and discriminated against, to the point that he was ready to walk out of the office and never return. However, Michael got between Oscar and the door and proceeded to prove that he had no problems with homosexuality.

After being called ignorant, insulting, and small, Michael tried to apologise to Oscar, and ended up planting one of the most awkward, uncomfortable kisses TV has ever seen. Michael wanted it burned into his co-workers' brains, and it most certainly worked for the audience too.

This was likely just as cringey for Oscar Nunez while acting the scene, as this was not written in the script, and was famously improvised by Steve Carrell. As painful as it is to watch, this has gone on to be one of the most iconic scenes in the show's long history.

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