Funny There's Some Ho Ho Ho's In The Pits Shirt
Not me, but a friend from high school. The guy is like a real life Michael Scott: cringe. He'll say a painfully stupid/awkward thing, and then he'll somehow top it. Seemingly no self awareness. Took me years to really appreciate the guy. What he lacks in comedic timing and self awareness, he makes up for with heart and determination. He seems to desparately want the approval of people, including (I assume) his parents.

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