I sent a few I regret, but nothing worth mentioning.

A friend, however, really screwed up. We were both working for a Fortune 100 company. She sat in a cube across from me. One day at lunch, she was reading email and LOL. I asked what was so funny. She offered to forward me a bunch of dirty jokes she had received in email. She fat fingered the address and ended up sending the mail to an admin in the corporate law department. The admin was not amused.

Pretty nasty jokes. The one I remember:

"What's the difference between doing 69 and driving in the fog?
When you're driving in the fog, you can't see the ********* in front of you."

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Behind every great man is a great woman. Behind every great woman is a great behind.