In a battle, my friend's Charmander was up against a Psyduck. The Psyduck was just standing there looking confused. Charmander used Ember, and instead of dodging, Psyduck just stared at the flames coming its way until it got hit and then started running around in circles. It was a really funny sight.
There was a battle where a Jigglypuff was fighting a Weedle. Jigglypuff started to sing its Sleep Song. Weedle, instead of falling asleep, started to dance to the song. It was so comical as it wiggled around while Jigglypuff just looked on in confusion.
A group of friends were having a Pokemon-catching competition. One of them had a Masterball. He was so overconfident that he boasted he could catch any Pokemon with it. But when he finally found a shiny Rattata, he got so nervous that he fumbled the Masterball and it rolled away down a hill. The Rattata just looked at him and scurried off. His friends couldn't stop laughing at his clumsiness.
I once heard about a trainer who was in a hurry to catch a Snorlax. He grabbed his Masterball but instead of throwing it properly, he tripped and the Masterball bounced off his head and landed right on the Snorlax. It was a very lucky and hilarious accident.
Well, there was this time a trainer accidentally sent out the wrong Pokemon. They meant to send out their Charizard but instead sent out a Magikarp. Magikarp just flopped around helplessly while the opponent's Pokemon was all confused, not knowing what to do. It was hilarious to watch the Magikarp's futile attempts at 'attacking' which was basically just more flopping.
I have a story about a shiny Eevee. A trainer was looking for a normal Eevee to evolve into a specific type. But then, he found this super cute shiny Eevee. At first, the Eevee was very playful. It would jump around and roll in the grass. When the trainer tried to catch it, it played tricks on him. It led him to a group of wild pokemon and then disappeared. The trainer was confused but also thought it was really funny.
Sure. There was a story where a Pikachu accidentally zapped itself while trying to show off its electric attack to a group of Pidgey. It ended up with its fur all ruffled and looking really silly.
One memorable story is about a Jigglypuff. It was singing its lullaby to make everyone fall asleep, but a Snorlax was already asleep and snoring so loudly that no one could hear Jigglypuff. Jigglypuff got so mad that it puffed up even more.
Once, I was at a concert. There was a couple in front of me who seemed to be having their own little dance party. They were completely out of sync with the music and each other. The guy was doing some really wild moves, and the girl was trying to be all elegant. It was a strange and funny sight. People around were trying not to laugh out loud, but it was really hard.
My friend and I were hiking in the mountains. We came across a family of deer. One of the fawns was really curious and started following us. It was so cute. We tried to shoo it away gently because we didn't want to disrupt it too much, but it just kept coming closer. Eventually, its mother called it back and we all had a good laugh about our little furry follower.