The disparity between their reactions based on what they thought was said. Let's say he said 'I like your hair' but she heard 'I like your air'. So she starts talking about how fresh the air is around her place. And he's just looking at her like she's lost it. That disconnect in understanding and the resulting odd conversation is really funny.
The funniest part is often the confusion that follows. For example, if he says he wants to 'hang out' at his place just to watch a movie and she hears 'hand out' as in give her something, she might show up expecting a gift. It creates an awkward yet hilarious moment.
I heard about a date where the two people went to an amusement park. They got on a roller coaster, and during the ride, the guy's false teeth flew out! He was so embarrassed at first, but the girl found it hilarious and they ended up having a great time searching for the teeth later. It's a story they still laugh about.
In the story about the girl and her cat, the cat's crazy chasing of the pennies was the funniest. It was unexpected and made the whole situation very comical as the cat seemed to think the pennies were alive or something.
A friend of mine went on a date to a park. They decided to have a picnic. But as soon as they sat down, a bunch of ducks came over and started stealing their food. They were chasing the ducks around, trying to get their sandwiches back. It was hilarious and they still talk about that date all the time.
One funny dating story is when a couple went on a hike for their date. The guy got lost even though he claimed to be an expert hiker. They ended up wandering around for hours. But in the process, they discovered a beautiful hidden waterfall and had a great time. So, it was a funny yet memorable date.
A friend of mine went on a date ice skating. He thought he was a pro but ended up falling on his butt every few minutes. His date was much better at it and had to keep helping him up. He said it was both funny and embarrassing.
A friend of mine matched with someone who said they were an astronaut. Turns out, they just worked at a planetarium selling tickets. It was so funny how they tried to make their job sound way more glamorous.
A friend of mine went on a date with a guy who took her to a horror movie. But during the movie, he was so scared that he screamed like a little girl and spilled his popcorn all over her. She was more horrified by his reaction than the movie itself.
The funniest part could be when the fisherman's expectations are completely subverted. For example, when he anticipates catching a big fish but instead gets something completely unexpected like an old shoe or a can. It creates a humorous contrast between what he hoped for and what actually happened.
If the story was about Joe Hill's attempts at a new hobby, like painting. The funniest part might be when he thought he had created a masterpiece but it actually looked like a child's scribbles. And when he showed it off to his friends with so much pride, their shocked and then amused expressions could be the funniest moment.
The unexpected things that happen because of the pulley. For example, if something is supposed to go up but goes down instead, or if an object attached to the pulley causes chaos in a funny way like hitting other things or people.