Have you ever sent or received a really embarrassing email by mistake?

No, but, I know someone who did. He took a photo of himself apres getting his rocks off (a nice close-up) and he meant to send it to his boyfriend (only). This was with his new cell. It ended up going to all of his family members, though, including his Mama in the nursing home.

Not guilty by reason of temporary insanity.

Guy to his girlfriend while on holidays……Having a great time, the place is brilliant, the weather is fantastic wish you were her………………. :-/ I heard about this one, not mine though some silly fool.. Lol….

Wasn’t a personal email, but at work I sent one to a customer that should have gone to a colleague, in which I was discussing their complaint and telling her what needed to be done. Thankfully it was a positive outcome for the customer and there were no repercussions but it could have been nasty under other circumstances. I’m now VERY caretul to double-check the email address before hitting Send.

Can’t recall receiving any particularly embarassing emails, but boy oh boy, I’ve sent some dandies. One I remember in particular —I inadvertently sent a boss-bashing email to my boss instead of to a fellow employee. I think I included a sentence about her being more attractive than bright, or something awful like that. All I could think to do was walk into her office and own up to it, explaining that I had only intended only to vent some frustration. She accepted the apology and there was no reprisal of any kind.

I have done that. It only said though” You have a sick sense of humor”. I got a reply. ” I never thought so” from a realitor I was dealing with. LOL. We joke and joke about it now.

Not really, but one time there is this guy I had a crush on in school, I msned him saying ” I love you! <3” I thought he would at least say something, but he didn’t even reply:/
Though in mind I was pretending that if he said something I would pretend it was supposed to go to my boyfriend, but it didn’t work:/

Once I texted something to Twitter instead of to my best friend. It wasn’t anything embarrassing, though; nobody even knew what the hell I was on about. Other than that, I’ve never done anything like that because I’m a little paranoid about it so I always double-check. XD (I’d just woken up and was extremely groggy and doofy still when my mistake did happen.)

Once I got a random text message from a stranger. It was, as @jjmah called it, “a nice close-up.” Ahem. I wrote back and asked who he was and found myself under an avalanche of profuse apologies. Apparently, my phone number is one digit away from his girlfriend’s. I told him it was no problem, everyone makes mistakes, and I’m sure his girl would enjoy the picture once he actually sent it to her. :D

oh man, sent a really embarrassing (sexualish) text to the wrong guy once… it was awkward but all i could do was laugh. oh well, shit happens!

I’ve sent text and text pics to the wrong recipient because I know several people under the same name I’ve been on intimate terms with in my celly. Because of the nature of our histories then they didn’t think it was too out of line but still… oops. At least the return replies were favorable ;p

I received an email once that was very embarrassing.