Tricky Riddles

tricky riddles
Tricky riddles will bend your brain! Challenge yourself and Can Leave Anyone Confused. 100+ Best Tricky riddles for you to trick everyone.

After a heavy Thanksgiving meal, the night watchman went to work. In the morning, he told his boss he had dreamed that a saboteur planted a bomb in the factory and that he felt it was a warning. The boss promptly fired him. Worker confused, Why boss fire him?

Asked by Patrik on 28 Dec 2025


A boy purchased a book from a bookkeeper and gave him $100.
The cost of the book is $50 but the bookkeeper has no change, so he gets the change from the next shop and returns the boy his $50.

After some time the next shopkeeper came with the $100 note and told the bookkeeper that the note was a fraud, so he took the money back.

How much loss did the bookkeeper face?

Asked by Sachin on 25 Dec 2025

Assume there are approximately 5,000,000,000 (5 billion) people on Earth. What would you estimate to be the result, if you multiply together the number of fingers on every person's left hand? (For the purposes of this exercise, thumbs count as fingers, for five fingers per hand.) If you cannot estimate the number then try to guess how long the number would be.

Asked by Sherlock on 24 Sep 2025


Jigsaw captured 100 people and make them stand in a circle and all these people are labelled as Person1, Person2, Person3... Person100. He made them play a crazy game in which Person 1 shot Person 2 and pass the gun to the next person and so on until one stands alive.

Which person will survive in the end?

Asked by Paul on 23 Sep 2025

500 women soldiers are arranged in an array of ten rows and fifty columns in accordance with their respective heights. Now, the tallest woman from each row is asked to move out in the front. From them, the shortest one is labelled as Alpha. They are then asked to resume their original position.

Now, the shortest woman in each column is asked to come out in front. The tallest among them is labelled as Beta.

Can you find out if Alpha will be taller or Beta?

Asked by Sachin on 16 Sep 2025

A man stands on one side of a river, his dog on the other. The man calls his dog, who immediately crosses the river without getting wet and without using a bridge or a boat. How did the dog do it?

Asked by Vinod on 05 Jul 2025


A man is sitting in a bar when a rich man sits next to him. He turns to the rich man and says, “Did you know I know almost every song that has ever existed?”

The rich man laughs. The man then says, “I bet you all the money you have in your wallet that I can sing a genuine song with a lady’s name of your choice in it. The rich man laughs again and says, “OK, how about my daughter’s name, Jamie Armstrong-Miller?” Minutes later, the man collects his cash and the rich man goes home cashless. What song did the man sing?

Asked by Sachin on 28 Jun 2025

Wednesday, Steve and Pam go to a restaurant to eat lunch. After eating lunch, they pay the bill. But Steve and Pam do not pay the bill. So…who does?

Asked by Ronit on 26 Jun 2025

Chef Andrea has to light the kitchen stoves to open her restaurant for the day. There are three stoves in the kitchen: A glass stove, a brick stove, and a wood stove. She only has one match. Which does she light up first?

Asked by Sachin on 24 Jun 2025


You’re out on the water and see a boat filled with people. You look away for a second and look back again, but this time you don’t see a single person on the boat. Why? Hint: The boat did not sink.

Asked by Sachin on 15 Jun 2025

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Crossword

The day before the 1996 U.S. presidential election, the NYT Crossword contained the clue “Lead story in tomorrow’s newspaper,” the puzzle was built so that both electoral outcomes were correct answers, requiring 7 other clues to have dual responses.