25 Hardest Riddles That’ll Make Your Head Hurt

Posted by , Updated on November 20, 2023

You’re thinking, “Does he really have 25 hardest riddles that’ll make my head hurt?” That answer to that riddle – yes, I do! Do you think you can solve some of the hardest riddles out there? I’ve searched high and low to find some of the most difficult riddles and I think I have found them! Now, I challenge you to figure them out without looking at the answers provided. Can you do it? I believe you can! So go ahead, pull up a chair and let’s have some fun. That is of course if you like riddles. If you don’t, this list might be a nightmare for you. Even if you do like riddles this list might be a nightmare because let me tell you…these riddles are not easy. So proceed at your own risk. Here are 25 hardest riddles you’ll never solve on your own.




Take off my skin – I won’t cry, but you will! What am I?


Answer: An onion.


What type of dress can never be worn?


Answer: Address


What word starts with the letter E ends with the letter E but only has one letter in it?


Answer: Envelope.


A man and his boss have the same parents but are not siblings. How is this possible?


Answer: He is self-employed. He is his own boss.


What comes once in a minute, twice in a moment, but never in a thousand years?

every minute countshttps://www.rd.com/funny-stuff/challenging-riddles/

Answer: The letter “M”


First, think of the color of the clouds. Next, think of the color of snow. Now, think of the color of a bright full moon. Now, answer quickly, what do cows drink?


Answer: Water

…you said milk, didn’t you?


How can the number four be half of five?


Answer: IV, the Roman numeral for four, which is “half” (two letters) of the word five.


What word in the English language does the following: the first two letters signify a male, the first three letters signify a female, the first four letters signify a great, while the entire world signifies a great woman. What is the word?


Answer: Heroine


You see a boat filled with people. It has not sunk, but when you look again, you don’t see a single person on the boat. Why?

boat peoplehttps://www.rd.com/funny-stuff/challenging-riddles/

Answer: All the people were married.


I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?

las vegashttps://www.rd.com/funny-stuff/challenging-riddles/

Answer: A map


You measure my life in hours and I serve you by expiring. I’m quick when I’m thin and slow when I’m fat. The wind is my enemy.


Answer: A candle


If you break me, I do not stop working. If you touch me, I may be snared. If you lose me, nothing will matter.

broken glasshttps://plentifun.com/hardest-riddle-ever

Answer: Heart


What does man love more than life, fear more than death; what does the poor have, the rich require, and what contented men desire; What the miser spends and the spendthrift saves and all men carry to their graves?


Answer: Nothing


Can you transform the word THINK into BRAIN while changing only one letter at a time in a manner that each of the word in the process is a real word?


Answer: THINK

Replacing N with C

Replacing H with R

Replacing I with A

Replacing K with T

Replacing C with I

Replacing T with N

Replacing T with B


Voiceless it cries and wingless flutters, toothless bites and mouthless mutters. What am I?


Answer: The wind.


Once you say my name I cease to exist. What am I?


Answer: Silence


You live in a place where six months of the year is mild summer and during the other six months, the mercury goes drastically down! You own a lake where there is a small island. You want to build a house over there and need to get some materials across there. You have no boat, plane or anything which you can use to transport them to the island. How will you solve the problem?

frozen lakehttps://www.kidspot.com.au/things-to-do/activity-articles/5-difficult-riddles-for-kids/news-story/bbfe6ffe6c453d245b6fc995aa136ad7

Answer: Wait for winter. The lake will freeze when the temperature drops.


Hurt without moving. Poison without touching. Bear the truth and the lies. Are not to be judged by our size. What are we?


Answer: Words


I have keys but no locks. I have a space but no room. You can enter, but can’t go outside. What am I?


Answer: A keyboard


I never was, am always to be. No one ever saw me, nor ever will. And yet I am the confidence of all, To live and breathe on this terrestrial ball. What am I?

thinking manhttps://plentifun.com/hardest-riddle-ever

Answer: Tomorrow / Future


If you look you cannot see me. And if you see me you cannot see anything else. I can make anything you want happen, but later everything goes back to normal. What am I?


Answer: Your imagination


What English word has three consecutive double letters?

I dont knowhttp://www.readersdigest.com.au/true-stories-lifestyle/thought-provoking/9-toughest-riddles-ever?page=6

Answer: Bookkeeper


What English word retains the same pronunciation, even after you take away four of its five letters?


Answer: Queue


A man is traveling to a town and comes to a fork in the road. If he goes left, he goes to the liars' village. If he goes right, he then goes to the village of truths - which is where he wants to go. However, he does not know which way is which. He doesn't have time to go both routes, so he approaches a stranger who is standing in the middle of the fork. The stranger says he may only ask 3 questions and he will answer them. The man asks, "Are you from the village of truths?" The stranger says, "Yes!" However, the man is still facing a dilemma: If the stranger was from the village of truths he can only tell the truth, but if he was from the village of liars, he would say he was from the village of truth. So then he asks the stranger, "Are you telling the truth?" The stranger says, "Yes!" But sadly this leaves the man in the same position as before. Can you figure it out?

traveling manhttps://plentifun.com/hardest-riddle-ever

Answer: The man asks the stranger the path back to his own village. If the stranger was from the village of truths, he takes him there. If he was from the village of liars, he will still take him to the village of truths as he would be compelled to lie.


I turn polar bears white And I will make you cry. I make guys have to pee And girls comb their hair. I make celebrities look stupid And normal people look like celebrities. I turn pancakes brown And make your champagne bubble. If you squeeze me, I'll pop. If you look at me, you'll pop. Can you answer this riddle?


Answer: Pressure

Photo: Featured Image - pxhere (Public Domain), 1. pixabay (Public Domain), 2. pixabay (Public Domain), 3. Peter, The inevitable queue for the Ladies toilets, here at Hay on Wye. Why does it always happen? There is acres of space for extra cabins and the long wait meant many women gave up (I heard them grumble) and had to sit in discomfort. Why don't they complain? Needless to say, there was no queue for the Gents., CC BY 2.0, 4. maxpixel (Public Domain), 5. maxpixel (Public Domain), 6. I, Satyakamk, ThinkingMan Rodin, CC BY-SA 3.0 , 7. Max Pixel (Public Domain), 8. Pixabay.com (Public Domain), 9. pixabay (Public Domain), 10. pixabay (Public Domain), 11. pixabay (Public Domain), 12. pixabay (Public Domain), 13. Pexels.com (Public Domain), 14. Pixabay.com (Public Domain), 15. Pixabay.com (Public Domain), 16. Pixabay.com (Public Domain), 17. Defense.gov (Public Domain), 18. maxpixel (Public Domain), 19. Shutterstock, 20. publicdomainpictures (Public Domain), 21. darknesslord (Public Domain), 22. maxpixel (Public Domain), 23. Pixabay.com (Public Domain), 24. Mabalu(photograph), Sarah Burton for Alexander McQueen (dress)., Ballgown by Sarah Burton for Alexander McQueen. Dress of the Year 2011, CC BY-SA 4.0 , 25. Paperxcrip: Helena Paffen, Light skin and hair, CC BY-SA 3.0