Well, I have said alot of embarrassing things and some even had positive results. Therefore, I am going to have to go with a text, that ended up with me and my friend fighting it out.
It was during class and he was texting a girl that I knew he liked but she wanted to take it slow. He just kept telling me about it " She is really direct and wants to take it slow, Im all cool with it but, dont know when to start speeding it up." Being a prick and wanting to 'help' my friend, I waited till he was away asking the teacher on how to do a question. I grabbed his phone from under his pencilcase and texted "Hey, Im really attracted to you and want to speed it up, no need to be frigid, phone sex would be a great start."
Now this is where I fucked up, the girls name is Mel (Mellisa) and right next to it on contacts was Mum. Yep, I sent it to Mum.
Moments later he returned and his phone vibrated. Picked it up and had the "wtf" look on his face. I tried my best to hold in the laughter then said "so what she say?" He just made me look at the screen and there it said "CALL ME -Mum"
Right there I knew I fucked up big time. I really dont want to type out the whole story but, yea, he has a mother that thinks sites like myspace and tagged is just a way for teenagers to view softcore porn etc.
In the end, our friends found out and we resolved the conflict. Till this day, we still remain good friends
Oh and he explained the situation to his girlfriend and they had a good laugh about it. So in a way I DID help

PS: wow, felt like typing a life story. If you read it, good for you *gives cookie*