A very memorable one was when our cleric tried to heal a poisoned character. But instead of using the right spell, he used a spell that made the character's skin turn bright purple and their hair stand on end. They looked like a walking, talking, purple - haired monster. And every time someone tried to touch them to reverse the effect, they got a small electric shock. It led to a lot of silly situations as we tried to fix it.
In a DnD session, we had a paladin who was overly confident. He charged at a group of trolls, shouting heroic phrases. But he slipped on a banana peel (left by our rogue for some reason) and landed right in front of the trolls. They just stared at him for a moment before he scrambled up and we all burst out laughing.
Once upon a time, in a DND session, our party of adventurers entered a mysterious forest. There were strange noises all around. We came across a talking squirrel. It told us of a hidden treasure but also warned of a giant spider guarding it. We decided to take the risk. As we crept closer, the spider emerged. But our wizard cast a sleep spell and it worked! We got the treasure and it was filled with magical items.
Once in a DND session, we were exploring an old, abandoned castle. As we entered the dungeon, strange whispers filled the air. My character, a brave knight, suddenly lost all control of his actions. The DM described my character turning on the party and attacking without any reason. It was a total nightmare as we had to fight our own teammate. We were all so shocked and it took a while to figure out how to subdue my character without killing him.
You can start by creating interesting characters. Think about their races, classes, and personalities. For example, you could have an elven ranger who is very shy but an excellent tracker. Then, decide on a starting location like a spooky forest or a bustling city. Another way is to start with a problem or a quest. Maybe the characters are hired to find a lost magical artifact.
Once, my character, a clumsy wizard, was trying to cast a simple light spell in a dark dungeon. Instead of just a small orb of light, he made a huge explosion of blinding light that not only illuminated the whole area but also scared the rats so much they ran right into the goblin guards, causing total chaos.
Once, our party's bard tried to charm a dragon with his music. He started playing this really wild tune. The dragon just looked at him like he was crazy for a moment, then started to sway along as if it was enjoying the show. It was hilarious seeing this huge, terrifying dragon getting into the music instead of attacking us right away.
One funny paladin DND story is about a paladin who was so dedicated to his code of honor that he accidentally challenged a very old and cranky tree spirit to a duel. The tree spirit was just sitting there, minding its own business, but the paladin misinterpreted some rustling of the leaves as a threat. The duel consisted of the paladin trying to swing his sword at the branches while the tree spirit just dropped acorns on his head. It was hilarious to see the paladin getting so frustrated.
During a DND campaign, my character rolled a Nat 1 for a stealth check. I was trying to sneak past a group of guards. Instead of being quiet, my character tripped over their own feet and made a huge racket. The guards immediately noticed and started chasing me. My friends' characters had to quickly come up with a plan to either fight the guards or create a distraction so I could get away. It was so funny because it was supposed to be a simple sneaking mission but turned into a chaotic chase scene all because of that Nat 1.