Because everyone can use a good laugh and share experiences you've had in roleplaying. To put it simply, share those moments that probably don't look great to the ones that posted, after a bit of hindsight. But will always be funny and something you laugh about. Now keep it to IC stuff. I could go on for eternity about the private or OOC stuff. But that's not as fun or memorable. With that brief/obvious explanation out of the way.

I'll start in sharing two quick particular experiences. Both with my roommate and his cousin, bless their souls, but they had a plethora of fail moments. So here's two of them with some simple context.

First, the roleplay was just the three of us. Each of us controlled three demi-gods that were shaping a new world. Backstory isn't important. The purpose was a battle/action roleplay where we would fight one another. Both of them we're itching to fight as soon as possible. So very early on, I described one of my gods wandering in a completely barren and dry desert oasis in scorching heat of daylight to scope out the area. My roommate really wanted to fight me, his three gods had the general powers of Light, Earth and Water. Do I even need to tell you which one sent given the topic at hand?

He sent his water god and challenged me to a fight to the death. Apparently, he missed the whole 'completely dry and barren' part (and the desert part). Which his exasperated screams over the phone, "WHAT DO YOU MEAN IT'S NOT A WATERY OASIS?" made it all the more hilarious. It was a miracle that that demi-god made it out alive. A moment I'll never let go. Wasn't even the last lopsided battle in that RP. (Pro-Tip, don't write you expose your only obvious weak point to launch a powerful attack, if your opponent is in easily range of it. Also, don't join a battle RP and expect no death.)

So the second one is also quite early into the story and happens to be his cousin's fault this time, we had a six person party. A simple D&D style quest adventure, everyone had just entered the small town that was about to get attacked by a group of bandits. So the group gathered in the middle of the town where they started causing trouble. So, the cousin's character who was a warlock decided to start the battle by threatening and instilling fear into them. He changed his ordinary human appearance, into something more demonic looking. One bandit cried out that he was a monster. He loudly called back in a unnatural voice. "I'm not a monster, I'm a devil!" He proceeded to laugh manically. Ah, teenagers and their writing. Good times...

The problem with this, is one of the other character's entire backstory is based on demons slaughtering his people. He also was a barbarian and mercenary paid to kill demons, and a stranger whom he hasn't met yet started calling out in the middle of the town. "Mwhahaha, I'm a devil." casting fire spells. So, it lead with a bastard sword impaling that character. His cousin was not pleased with this action. But basically everyone else laughed their asses off. Maybe not the best way to introduce yourself. Edge writing, on top of being embarrassing to read often leads to embarrassing results. Sometimes, a quick and instant death...

There you have it. Well, I found them funny. I'll post a few more, if anyone else cares to keep the stories coming. Have something better? Do tell. ;3