Worst thing you have ever said to someone?

I told my friend he was doomed to get an incurable disease. He got herpes less than month later.

 

"Go fuck your pop"

Less than a week after the girls grandfather died.

Do not play with fire if you do not want to get burned.

 

Thats fuckin cold. i would have whooped your ass after he died.

 

The last words me and my ex shared. She said 'I still love you' and I said 'I nothing you'. Apparently that hurt her quite a lot xD

 

I cant recall really. I mean I'll be blunt and rude if im pissed off at someone, but I dont really sit there and call them down.

 

i kissed ur girl brah , the dude was a dik tho..

 

When I was very young I said to a half white / black kid, "whatup *****!?" And tried to execute the boyz in the hood handshake.

Backfired pretty hard.

 

Fuck you man

 

I fucked your mom. I fucked her real hard.

Then I fucked your sister after I fucked your girlfriend.

Then fucked your mom again.

 

In grade 9 my ex said she was getting drunk and I said 'Stay green smoke weed' and she called me a fag so I called her a drunk failure. Not the worst I've said but I can't remember

But yeah she's actually one of the biggest failures I know and she knows it haha

 

I'm not proud of this one.
I have a friend a little on the slow side. He's nice, and funny, can trust him allot, but he can't really read or spell.

So I was talking with someone else, and he just kept interrupting 'how do you spell this what's that word?'
I kept trying to have my conversation and he continued asking shit, and I ended up blurting "Learn how to read!"

Aw man, I felt like shit. I apologized, and that shit was years ago.
But man, what a dick move.