[Egao, Egao Everywhere]

I think the most hilarious moment I experienced in RPing was when my character in PRE was paired with Red's mom. I guess it wouldn't make sense if you weren't there but it was funny for so many reasons.

[SIFR]

I ran a Sailor Moon site with a pitiful attempt at a battle system. We were doing the awakening for the Knight of Mercury (basically the male equivalent of Mercury but now a days every single Sailor Moon site has a Knight... THEY DIDN'T BACK IN MY DAY WTH GUYS) and I pitted a monster that closely resembled Tangela from Pokemon at him, that attacked him in the shower by coming through the pipes.

The character proceeded to curse repeatedly, run down the stairs to the kitchen in nothing but a towel, open the fridge door and proceed to try to feed it by throwing food at it. The food did minimal amounts of damage to the monster's body, then managed to catch him and nearly kill him. Instead of the cat that was in the thread giving him the transformation item, Knight of Mercury proceeds to pull the monster's own tentacles out of his chest and stab the monster with his own tentacles.

So now to this day, we still remember that the Knight of Mercury defeated the monster with a link of Polish sausage, a head of lettuce and his own tentacles.

Oh, and as he was throwing the lettuce, he decides to yell "LETTUCE SETTLE THIS LIKE REAL MEN."

I died.

[Starry Neko]

I know this is only funny to like two people, but I had this creature that was just weird. He looked like a fourteen year old, was actually god knows how old, and had the mental capacity of a four year old with the social ability of a spacey goldfish. Well my character was chasing a spider in the library, and he was crawling around after it like a ditz. Well he ended up under one of the library tables next to the other character and then got distracted because the boy moved- so my character just ended up scaring the living crap out of him by petting the stranger's legs and commenting about how he had pretty pants.

I cracked up to the point of tears reading her reply to that. I couldn't stop laughing for like...ten minutes straight. I think I literally broke her character's brain and I enjoyed it to the point of sadistic glee.