What was the most embarrassing that happened to you or someone you know?

#1

My brother was pranking a friend of his, who happened to be a girl but who he decidedly claimed he did "not like."
He tried to set up his email so that it automatically sent her a "blocked" message every time she tried to contact him. Only thing was, he set it up wrong and it ended up going to EVERY SINGLE CONTACT he had.
To make it even better, her name was on it, and since all his friends knew her too they were very confused.
Talk about awkward.
We laughed at him so hard.

He married the girl two years later.🤷‍♀️🤣

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#2

Me and this guy were friends, and my friends were always saying we like each other, we always denied. Then out of the blue he asks me if I wanna be his gf, i'm like umm idk. He kept asking and asking and one day he just stopped and got a different gf. I was relieved, but then realized he still likes me, and we sit next to each other in homeroom. Sooooo ongoing awkwardness.

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