25 Hardest Riddles That’ll Make Your Head Hurt

Posted by , Updated on January 9, 2019


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.


Subscribe to List25


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”

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

SEE ALSO: Biggest Rip Offs That You've Probably Been Tricked Into Buying »

NOW WATCH: 25 Most Dangerous Kids' Toys Ever Made

Subscribe to List25
Show Us Your Love
Join Over 2 Million+ List25 Fans