The 10 Hardest Riddles You’ll Ever Hear

If you want to see just how smart you are, you can put your brain to the test by reading different riddles. Sure, there are plenty of riddles that are easy to figure out, but there are even more that will have you stumped for hours. If you want to see how talented you really are, here are a few of the hardest riddles you’ll ever hear.

1. Many have heard me, but nobody has seen me, and I will not speak back until spoken to. What am I?

“An echo.” Think back to the last time you yelled out to someone and heard your own voice echo through the room. It obviously only happens after you speak, which means an echo cannot speak back until it is spoken to.

2. A window cleaner is cleaning a window on the 25th floor of a skyscraper when, suddenly, he slips and falls. He has no safety equipment and nothing to soften his fall, and yet he is not hurt. How can this be?

“He was on the inside.” The riddle never says the man was cleaning the outside of the windows. He was actually on the inside of the building, cleaning the windows from that side. That means he was never in any real danger.

3. What has only two words, but thousands of letters?

“A post office.” This questions tricks you, because it makes you think that “letters” are referring to the letters of the alphabet. Of course, they’re simply referring to the types of letters you stick in the mailbox and seal with a kiss.

4. I am a cold man without a soul. If there is warmth in me, it slowly will kill me. What am I?

“A snowman.” Unfortunately, snowmen aren’t going to last forever. As soon as it gets warm out, they’re going to disappear.

5. What is as big as you are and yet does not weigh anything?

“Your shadow.” Sometimes, your shadow looks like it’s even bigger than you are. Of course, that doesn’t change the fact it weighs less than you do.

6. When you have me, you feel like sharing me. But, if you do share me, you don’t have me. What am I?

“A secret.” It’s hard to keep a secret, especially if it’s a juicy one. Of course, as soon as you tell someone your secret, you can no longer consider it a secret. Once one person knows, the whole world might as well know. There’s no longer any way for you to keep it from escaping.

7. The person who makes it has no need for it. The person who purchases it does not use it. The person who does use it does not know they are. What is it?

“A coffin.” Unfortunately, the person who ends up using a coffin will never actually know they’re using it. Meanwhile, the person who creates it and the person who purchases it are never going to use it themselves. The whole thing sounds like a waste when you put it that way.

8. What question can you never answer yes to?

“Are you asleep yet?” If you answer the other person, then you’re clearly not asleep yet. If you were, then the only answer you gave them would be the sound of your snoring.

9. I take what you receive and surrender it all by waving my flag. What am I?

“A mailbox.” This is a hard one, because when you think about someone surrendering with a flag, you either think of a boxing match or a war. Of course, the answer is a lot more simpler than that!

10. What flies when it’s born, lies when it’s alive, and runs when it’s dead?

“A snow flake.” Think about it. When a snowflake is first created, it falls from the sky. After that, it rests in the grass for a while until it melts. When it finally disappears, it’s like it has just run away.


What do you think is the greaest riddle ever created?





Holly Riordan
Holly Riordan
Holly is an aspiring sci-fi writer who currently writes lifestyle articles for All Women Stalk and News Cult. She's a fan of comedy movies, ridiculous puns, and is the owner of a pup named Ferris (last name Bueller).