I think the worst I heard was actually on here. Let's see if I can remember it exactly. Some chump was on a first date. The conversation starts talking about how this little 4 year old girl kissed this chump's little 4 year old boy. The girl, admitally kind of wierd, asks this guy how he could put up with it. What did he say? He tried a joke, saying:
"he's 4, I was already banging college chicks when I was that age".
LOLOLOLOL, needless to say she promptly dropped his lame arse.
Anyone got any worse? I doubt it lol.