These riddles are perfect for a mental workout! They blend humor and wit with a dash of logic. I enjoyed going through them—some are classic, while others are refreshingly clever. I can see these being a big hit for game nights or a fun challenge among friends.
Which riddle did you find the most challenging? The parachute and “Happy Birthday” ones have that sneaky twist that really stumps people! Let me know if you’d like any help crafting more riddles or adding a twist to an upcoming game night—I’m here for all the brainstorming fun!
Poor Man Wakes up One Morning and Finds His Late Father’s Old Trailer in His Backyard
One morning, a poor man is stunned to wake up and find his father’s old trailer in his yard with a note from his older brother — but the despised inheritance ends up making his fortune.
When Mark Kendrick’d first married, it looked as if life would run smoothly. He and his wife Sally had a good job. But then back in 2008, his wife lost her job as a chef when the restaurant she worked in closed down.
Left with a huge mortgage, two children, and one salary, the Kendricks had struggled. In 2019 when Mark’s father pa::ssed away, his estate — which was substantial — had all gone to his brother, Jim. It seemed that Mark just couldn’t catch a break.
Mark never told anyone, even Sally, but the conditions of his father’s will had hurt him deeply. Mark was the younger brother by nearly 20 years and the child of his father’s second marriage.
He understood that the company and the big house his father had lived in had once belonged to Jim’s deceased mother and were his by right — but Mark had thought his dad would leave him some token of his esteem.
When Mark was still a child, his father had often played hide-and-seek games with him. The little boy would often find a little treat under his pillow with a note — chocolate or a piece of candy — and the note always said: ‘Daddy loves you, Mark.’
They’d go off on vacation — Mark, his mom, and his dad — on their old trailer. His half-brother, Jim, would never go. He’d always turn up his nose at their ‘trashy trailer’ and go off with his fancy college friends.
The trio would drive around the back roads of America stopping whenever they fancied a town’s name, and the first meal they made was always his dad’s spicy clam chowder.
For Mark, those vacations were his fondest memories of his childhood, and they had ended when his mother pass::ed away, a victim of can::cer when Mark was fifteen. After that, the trailer just sat in the backyard.
Our family’s memories and the good times we spent together are the most precious things we have.
Mark’s dad had withered away to a shadow of his former self and became almost a recluse. In his last years, he refused to see anyone at all, even his sons and grandchildren.
Then, two years after his dad’s pa:ssing, Mark woke up to find the old trailer parked in his driveway! He immediately phoned his brother. “Jim, what’s going on?” he asked. “You left the trailer here?”
His brother was abrupt. “The old man wanted you to have that piece of junk,” he said. “And it’s taking up space I need. So you take it and throw away your own trash!”
“Jim,” Mark asked quietly. “Why can’t we be friends?”
“You ask me why?” asked Jim bitterly. “He loved you more than he ever loved me, he spent more time with you on that stupid trailer than he ever did with me. Tha’s why!”
Sad Mark hung up the phone, then he went outside and climbed into the old trailer. It was sadly neglected and would need a lot of work before it could be used again.
Mark sat on his old bed and tested the mattress. He’d have to get a new one. Then, out of old habit, he stuck his hand under the pillow. To his surprise, he felt something there!
There was an envelope under the pillow with his name on it! He opened it and found a bank book for an account with a balance of over $60,000! In the envelope was a recipe for his dad’s chowder, and a note.
The note read: “My dear Mark, this recipe and the memories of the good times we shared are all I have to leave you. I hope this money will come in handy. It’s not much, but it may help to smooth your way. Remember me. Daddy loves you, Mark.”
Mark had tears in his eyes. He took the bank book and showed it to Sally. “That’s not bad…” she said. “It’s not the millions that Jim got, but it will help. You can sell that old trailer too. That should bring in a little more money.”
Mark was in shoc::k. “I’m not selling my dad’s trailer!” he cried. “That’s out of the question!”
“Well I don’t want that piece of junk just sitting in the front yard!” cried Sally crossly.
Mark sat on the front porch looking at that trailer for hours. It certainly needed a lot of work… Then he pulled his dad’s recipe out of his pocket and stared at it. “Sally!” he cried. “Come here! I have an idea!”
“What is it, Mark?” she asked.
“You know how you always said you wanted your own restaurant?” he asked excitedly and pointed at the old trailer. “There it is!”
“Are you mad?” gasped Sally.
“No!” Mark said. “Listen, we transform that old trailer into a mobile restaurant/ food truck. We make that amazing clam chowder of my dad’s… We’ll paint it bright, happy colors and string up lights…”
“That could work,” said Sally thoughtfully. “If we can afford the licenses…”
They could and they did. Pretty soon, people were coming from all over the city to eat Pop’s Chowder, making Mark give up his job to help Sally. They started a franchise, and before long, there were Pop’s Chowder food trucks all over the state.
Mark was very happy. His father’s memory was honored every day, with every bite a satisfied customer took of that amazing clam chowder. And thanks to that legacy, he was taking good care of his family.
Mark called Jim and invited him and his family to join them for a family lunch at the old refurbished trailer. Jim came and ate the chowder and the two brothers made peace, just as their father would have wanted.
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