So I participated in a radio show this morning, people were calling in about the most embarrassing email they ever sent. There were a lot of them, about sending nude photos to the boss, venting about the boss and accidentally sending it to the boss instead of coworkers, etc.
Mine on the other hand wasn't an email but an instant message, a few years ago when I was trying out the online dating thing... I was talking to 2 different guys at the same time and was having a hard time deciding which way to go, but hey, I was pretty newly single and wasn't in any rush to decide...
I was chatting with both guys one night and a friend of mine as well, Guy #1 and I were having a really nice conversation and Guy #2 was flirting and being his normal pervy self. I went and copied the conversation Guy #1 and I were having, and went to my task bar at the bottom of the screen to open the messenger box to my best friend, Clicked her name, and without hesitating pasted and sent the conversation. About 5 seconds later I realized that instead of HER message box popping up, it had brought up the message box of Guy #2.
Needless to say, Guy #2 wasn't in the picture much longer, and Guy #1 is now my husband :)