Like horrible character mistakes that ended up providing a lot of entertainment. Or a series of mistakes that got the party killed but had you all laughing your butts off.

We just recently switched to pathfinder and our rogue forgot to put points into perception (the new detect all skill). He couldn't detect traps or anything else at all. :D We made fun of him in character the whole time. Asking him if he knew any rogues we could hire, etc. The silliness culminated when we needed him to steal a rowboat from a simple peasant.

He checked for traps, and unlocked the boat. Then he had to break into their house for the oars. Very simple DCs (like 5s and 10s) ...he failed. The peasant shot him with a crossbow and they both freaked out. He grabbed the oars and ran. We all pretended not to know him. He jumped into the row boat and started paddling furiously as the guards were called...The boat was trapped...he heard a loud jingling and ruckus as he noticed the boat had a thin line with bells tied to it on the docks that he was now dragging noisily behind him :D

It was quite amusing, perhaps you had to be there though :)