Mayukh Saha
Mayukh Saha
November 2, 2023 ·  5 min read

20 tricky riddles that are sure to stump you!

Tricky riddles are fun for the whole family. While most of us remain glued to our phone screens nowadays, it might be a good idea to come out of that shell and actually try something stimulating. Who knows- we may even get something positive out of it. So, here are 20 of the trickiest riddles from around the web that could make you think. Do you believe you are capable of solving them? Let’s see!

20 Tricky Riddles That Will Make You Think!

1. The Cement Room

Riddle: If you are stuck in a cement room with no means of escape, except a table and a mirror, how will you escape?

Answer: You look in the mirror and see what you saw, take the saw, and cut the table in half. Two halves make a hole- jump through the hole and you’re out.”

2. A Tricky Riddle For The Tricky People

Riddle: What can you sleep on, sit on, and even brush your teeth with?

Answer: Well, it is just a bed, a chair, and a toothbrush, isn’t it?

3. A War of the Words

Riddle: What always has four letters, sometimes has nine letters, but never has five letters?

Answer: If you look carefully, this riddle is an observation, rather than a question. Hence, it has no answer.

4. Eternal Beginnings

Riddle: I am the beginning of eternity and the end of time and space. The start of every end and the end of every place. What am I?”

Answer: This is quite simple- for it is the letter E.

5. Breakfast at Riddles

Riddle: “It’s 7 am. You are asleep and there is a sudden knock on the door. Behind the door are your parents, who came to have breakfast. In your fridge: bread, milk, juice, and a jar of jam. To answer, what will you open first?”

Answer: Since you are still asleep- you will be opening your eyes first. 

6. No Mouth, And Yet Words Flow

Riddle: “I speak without a mouth and hear without ears. I have no body, but I come alive with the wind. What am I?”

Answer: Speak into a ravine, and it would be the echo you listen to. 

7. Men In Masks

Riddle: “A man leaves home on foot one evening, makes three left turns and arrives back home to find two masked men waiting there. Who are they?”

Answer: Time for MLB fans to shine- for the masked men are the umpire and the catcher. 

8. Cabin in the Woods?

Riddle: There is a cabin in the woods. There are no footprints around the cabin. There are seven people inside that are all dead. They all died at the same time. There is no one else in the cabin. How did the people die?”

Answer: This is an airplane cabin- which crashed, unfortunately.

9. No Siblings

Riddle: A man in prison has a visitor. Afterward, a guard asks the inmate who the visitor was to him. The inmate replies: “Brothers and sisters I have none, but that man’s father is my father’s son.” Who was the visitor to the inmate?”

Answer: It was his son who came to meet.

10. Row, Row, Row Your Boat

Riddle: “Four men were fishing in a boat on the lake. The boat turned over and all four men sank to the bottom of the lake. And yet, not one single man got wet. How can this be?”

Answer: None of them were bachelors, so no single men were harmed. 

11. Bat and Ball

Riddle: “A bat and a ball cost $1.10 in total. The bat costs $1 more than the ball. How much does the ball cost?”

Answer: Just a meager 5 cents.

12. The Man Who Has It All

Riddle: The man who made it sold it.
The man who bought it did not use it.
The man who used it did not know it.
What is it?”

Answer: Sadly, it is a coffin. 

13. Box Of Treasures

Riddle: “A box without hinges, key, or lid, yet golden treasure inside is hidden. What is it?”

Answer: It is an egg.

14. Thirteen Hearts Why?

Riddle: What has 13 hearts but no other organs?

Answer: A deck of playing cards

15. The Vanishing Door?

Riddle: When is a door not a door?

Answer: When it is ajar.

16. Railroad Dilemma

Riddle: Railroad crossing, look out for the cars. Can you spell that, without any R’s?”

Answer: It is quite simple- T H A T.

17. It’s Cowboy Time!

Riddle: “A cowboy rides into town on Friday stay for three days and leaves on Friday. How did he do it?

Answer: In a similar vein to Robinson Crusoe, he named his horse Friday.

18. “I am NOT Your Father, Luke!”

Riddle: I am your father, but you are not my son. Who are you to me?”

Answer: You are my daughter.

19. Is This The Last Place You Looked?

Riddle: “How is it possible to always find what you’re looking for in the last place you look?”

Answer: If you find what you are looking for, then you would stop looking, so it would be in the last place you looked.

20. The American Doctor

Riddle: “A man and his son are in a terrible accident and are rushed to the hospital in critical care. The doctor looks at the boy and exclaims ‘I can’t operate on this boy, he’s my son!’ How could this be?”

Answer: The boy’s mother is the operating doctor.

So, did you escape the manipulations of the tricky riddles and find the answer? Great job! If you have more riddles that you want to share, write to us below!

This article originally appeared on Tiffy Taffy and has been republished here with permission

Want to try your luck some more? Here are some more tricky riddles you might enjoy: