http://omegle.com/ is probably one of the funniest sites I've seen in awhile. Pretty simple premise you click start chat and you are given a random person to talk to.
"Stranger: what football team do you support?
You: Linux ?
Stranger: who are they
You: they are a very secure team great defensive play
Stranger: where are you from?
You: From a place called Ubuntu small village"
The funniest moment I've had