Questions And Riddles 99% Of People Probably Can’t Solve

Riddles can be a great way to pass time on a boring road trip, or to test the waters of your pool of friends and see which of them is the smartest. Hard riddles can take the shape of anything from simple questions to paragraph-long logic problems that are best done with some graph paper and one of those giant pink erasers. Some of the impossible riddles collected here are sure to break your brain for at least a week, but once you solve them you’ll feel like the smartest person on the planet. FYI, if you want to try your hand at these questions most people can't solve without any help, don’t read the spoilers and answers written below every riddle.

Some of the hardest riddles and brain teasers are incredibly simple questions that have been around for years. In the time that it’s taken to find the Higgs Boson, build affordable electric cars, and hack an iPhone, the world is still having trouble figuring out who had Einstein’s fish. If you’re someone who likes to relax with a nice mystery, these hard brain teasers are the perfect way to spend an afternoon (or longer). Your IQ might even go up a few points, who knows?! If you think you’re ready, start digging into these questions and riddles that most people can’t solve.

  • Return To Sender
    Photo: Luyen Chou / flickr / CC BY 2.0

    Return To Sender

    If you eat me, my sender will eat you. What am I?

    To solve this you have to think about adjectives for "send": throw, give, cast, etc. What do you cast? If you guessed a fishhook, then you figured out the answer.

  • The Most Reliable Business
    Photo: Charles Chusseau-Flaviens / Wikimedia Commons / Public Domain

    The Most Reliable Business

    The man who makes it doesn't want it, the man who buys it doesn't need it, and the man who needs it doesn't know it yet. What is it?

    This riddle probably came to prominence during a world war, when the looming inevitability of mortality was around every corner. Quickly put yourself in the shoes of the man who doesn't know he'll be needing "it" and you realize that the answer is a coffin.

  • 10 Horses
    Photo: Francis Storr / flickr / CC BY-SA 2.0

    10 Horses

    How do you fit 10 horses into nine stalls?

    This riddle is more visual than some of the others, and the answer lies in actually typing out "ten horses" and getting creative with the concept of a stall: [t][e][n][h][o][r][s][e][s].

  • The Worst Four-Letter Word
    Photo: Moyan Brenn / flickr / CC-BY 2.0

    The Worst Four-Letter Word

    This four-letter word is always done tomorrow. We’re out of tea, the ultimate sorrow! Without the eye, you owe me some money. No sugar, no nectar, no sweetness, no honey. Four-letter word, if by chance you choose, you can never win, you can only lose! What is the four-letter word?

    Let's break this down into some simpler language. What four-letter word carries the cliche of always starting tomorrow? A diet. But what about the other clues? Diet without the "T" is "die," the ultimate sorrow. Diet without the "I" is a phonetic-ish spelling of "debt." And if your diet is a success, it means you've lost weight.

  • Age Ain't Nothin' But A Number
    Photo: robin robokow / flickr / CC BY 2.0

    Age Ain't Nothin' But A Number

    How is Barry 10 years old in 1870, but only five years old in 1875?

    Barry was born in 1880 BCE.


  • Up The Down Chimney
    Photo: grassrootsgroundswell / flickr / CC-BY 2.0

    Up The Down Chimney

    What can go up a chimney down but can't go down a chimney up?

    Apparently when this riddle was thought up, losing umbrellas via the chimney was a real problem. If you haven't figured it out yet, a closed umbrella can go up a chimney, but an open one can't go down.