100 Hard Riddles For Teens That Will Challenge You [Free Riddle Cards]

Last Updated on February 14, 2024 by Michele Tripple

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Do you think you have what it takes to solve the toughest riddles out there? Well, get ready to put your brain to the test with these hard riddles for teens! These riddles will challenge your critical thinking skills and require you to think outside the box.

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What starts with an E, ends with an E, but only contains one letter? The answer to this riddle may be easy for some, but don’t let that fool you. These hard riddles for teens only get more complicated from here!

But don’t worry; solving these riddles isn’t just about being smart. It’s also about having a sense of humor and being able to think creatively. So get ready to laugh your way through these challenging riddles and prove to your friends that you’re the ultimate riddle master!

If you want to challenge yourself further be sure to check out our logic riddles and our 75 Best Confusing Riddles.

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hard riddles for teens

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  • An Uber driver is going the opposite way down a one-way street. He passes five policemen along the way, none of which stops him. Why not? Because the Uber driver was walking.
  • What has 13 hearts, but no lungs or stomach? A deck of cards.
  • If you are running in a race and you pass the person in second place, what place are you in? Second place.
  • During which month, do people sleep the least? February. It’s the shortest month, with the fewest nights.
  • What should you break before you use it? An egg.
  • What gets sharper the more you use it? Your brain.
  • What can you hear but not touch or see? Your voice.
  • I call the trees my home, yet I never go inside. If I ever fall off the tree, I will surely be dead. What am I? Leaves.
  • I am the sweetest and most romantic fruit. What am I? Honeydew.
  • I have no doors, but I have keys. I have no rooms, but I have a space. You can enter, but you can never leave. What am I? A keyboard.
  • What has a thumb but no fingers and isn’t alive? A mitten.
  • What is full of holes but still holds water? A sponge.
  • I have hands, yet I cannot shake your hand. I cannot give you a high five, and I have no fingers. What am I? A clock.
  • Born in an instant, I tell all stories. I can be lost, but I never die. What am I? Memories.
  • What do you find at the end of the line? The letter “e.”
  • What is made of water, but if you put it into water will die? Ice.
  • 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 greatness, while the entire world signifies a great woman?  Heroine.
  • I live in the winter, but I die in the summer. My roots grow upward. What am I? An icicle.
  • Name three consecutive days that aren’t the names of the days of the week. Yesterday, today, and tomorrow.
  • What fruit is always sad? The blueberry.
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  • What can go up a chimney down but cannot go down a chimney up? An umbrella.
  • I’m tall when I’m young, and I’m short when I’m old. What am I? A candle.
  • People walk in and out of me. They push, and I follow. When they walk out on me, I close up. I wait for the next person to walk into my life and then I open up again. What am I? An elevator.
  • What is lighter than a feather but can’t be held for a long time? Your breath.
  • If an electric train is traveling south, which way is the smoke going? It’s electric. There is no smoke!
  • They are many and one; they wave and they drum. You take them with you everywhere. What are they? Your hands.
  • How can a man go eight days without sleep? He sleeps at night.
  • You walk into a room with a match, a kerosene lamp, a candle, and a fireplace. Which do you light first? The match.
  • What has a bottom at the top of them? Your legs.
  • What do teens say when they have trouble in their math class? “I can’t even.”
  • What gets wetter and wetter the more it dries? A towel.
  • The person who makes it does not need it. The person who buys it has no use for it. The person who uses it can neither see nor feel it. What is it? A coffin.
  • What kind of room has no doors or windows? A mushroom.
  • What kind of tree can you carry in your hand? Palm.
  • You can’t keep this until you have given it? A promise.
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  • What is so delicate that saying its name breaks it? Silence.
  • What has 13 hearts but no other organs? A deck of cards.
  • There was a greenhouse and inside the greenhouse, there was a white house. Inside the white house, there was a red house. Inside the red house, there were lots of babies. What is it? A watermelon.
  • Two fathers and two sons went duck hunting. Each shot a duck, but they shot only three ducks in all. How come? The hunters were a man, his son, and his grandson. 
  • If you have me, you want to share me. If you share me, you haven’t got me. What am I? A secret.
  • You can drop me from the tallest building, and I’ll be fine. But if you drop me in the water, I die. What am I? Paper.
  • Alcohol makes me thrive and multiply, yet water will kill me. What am I? Fire. 
  • They come out at night without being called and are lost in the day without being stolen. What are they? The stars.
  • People all over the world come again and again to see me. Most people spend years with me. I am able to make you smarter and wealthier too. What am I? School.
  • I am a term used to confirm. But take away my front and my face, I become known as human avarice. What am I? Agreed. 
  • A girl is sitting in a dark house at night. There aren’t any lamps or candles lit. Yet she is reading. How? The woman is blind, and she is reading braille.
  • Tuesday, Sam and Peter went to a restaurant to eat lunch. After eating lunch, they paid the bill. But Sam and Peter did not pay the bill, so who did? Their friend, Tuesday. 
  • All five sisters are busy. Ann is reading a book, Rose is cooking, Katy is playing chess, and Mary is doing the laundry. What is the fifth sister doing? She’s playing chess, of course!
  • A boy and an engineer were fishing. The boy is the son of the engineer, but the engineer is not the father of the boy. Then who is the engineer? The engineer is the boy’s mother.
  • While a cat was outside, it began to rain. The cat couldn’t find any shelter and got completely soaked. However, not a single hair was wet. How could this be? It was a hairless cat.
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  • There are five houses. A blue house, a pink house, a yellow house, a red house, and a greenhouse. The blue house is made of blue bricks. The pink house is made of pink bricks. The yellow house is made of yellow bricks. The red house is made of red bricks. What is the greenhouse made of? Glass. It’s a greenhouse.
  • What did the troubled math book say to the calculator, puzzle, and dictionary? “I have too many problems.” 
  • Why can’t you hear a pterodactyl in the bathroom? Because it has a silent pee. The past, present, and future walked into a bar. It was tense.
  • Where does Christmas come before Thanksgiving? The dictionary. 
  • How can one be 16 years old but celebrating their fourth birthday? Someone born on February 29. 
  • I run, it runs. I stop, it still runs. What is it? A watch. 
  • I speak without a mouth and hear without ears. I don’t have a body but I come alive with wind. What am I? An echo. 
  • I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I? A map. 
  • Why is Europe like a frying pan? It has Greece on the bottom.
  • How can you go 10 days without sleep? You sleep at night. 
  • What five-letter word becomes shorter when you add two letters to it? Short
  • A girl fell off a 50-foot ladder but didn’t get hurt. How come? She fell off the bottom rung. 
  • Runs smooth, can hit hard or soft. Loves to fall, but cannot climb. What am I? Rain.
  • What number has all its letters in alphabetical order when spelled out? Forty.
  • You throw away my outside, eat my inside, then throw away the inside. What am I? Corn on the cob.
  • You’re in a race and you pass the person in second place. What place are you in now? Second place.
  • What has 13 hearts, but no lungs or stomach? A deck of cards.
  • An Uber driver is going the opposite way down a one-way street. He passes five policemen along the way, none of which stops him. Why not?Because the Uber driver was walking.
  • Two fathers and two sons are in a car, yet there are only three people in the car. How? They are a grandfather, father, and son.
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  • While a cat was outside, it started to downpour. The cat couldn’t find any shelter and got completely soaked by the rain, yet not a single hair was wet. How could this be? It was a hairless cat.
  • You are in a dark room with a box of matches. Nearby are three things: a candle, an oil lamp and a log of firewood. Which do you light first? The match
  • The person who makes it has no need of it, and neither does the person who buys it. But the person who uses it can neither see nor feel it. What is it? A coffin.
  • A man shaves many times during the day, but at the end of the day, he still has a beard. How is this possible? The man is a barber. 
  • If you have it, you don’t share it. If you share it, you don’t have it. What is it? A secret.
  • What has no beginning, end, or middle? A doughnut. 
  • This vehicle is spelled the same from the front as well as from the back. What is it? A racecar. 
  • If there are three apples and you take two, how many do you have? Two.
  • A cowboy rode into town on Friday. He stayed in town for three days and rode out on Friday. How was that possible? Friday was the name of his horse.
  • Tom is younger than Dave but older than Jill. Lou is older than Sally who is older than Tom. Dave is older than Lou. Who is the middle child? Sally.
  • Two people were playing chess and both won. How did this happen? They were playing against other opponents. Chess is also one of the genius brain boosters for kids you can do together.
  • What eight-letter word remains a word as you keep removing one letter from it? Starting.
  • It has four fingers and a thumb but isn’t alive. What is it? A glove.
  • What is heavy going forward but not going backward? Ton.
  • I call the trees my home, yet I never go inside, and if I ever fall off the tree I will surely die. Leaves.
  • What goes up and never comes down? Your age. 
  • What can go through glass without breaking it? Light. 
  • I start in little but I end in full; you’ll find me in half and complete. The letter “L” 
  • Here’s a list of sports: golf, darts, tennis, cricket, football, badminton. Which should come next: archery, boxing, squash, gymnastics, or baseball? Gymnastics.
  • What question can you never answer yes to? Are you asleep?
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  • What comes up to let us go, or goes down to make us stay? An anchor
  • There is an electric train that is headed towards the east. So, where does the smoke go? There is none: An electric train produces no smoke.
  • What word is always spelled wrong? Wrong.
  • I am an odd number. Take away a letter, and I become even. What number am I? Seven.
  • I am a ball that rolls but can’t bounce or be thrown.What am I? An eyeball.
  • I am the only organ that named myself. What am I? The brain.
  • A girl buys a dozen eggs and, on the way home, all but seven break. How many eggs are left unbroken? Seven.
  • Which word is least like the others? Third, fourth, fifth, sixth, seventh, eighth, or ninth? Third.
  • A farmer has a bag of corn, a hen, and a fox. He has to cross a river, but his boat is only big enough to carry one thing with him. If the hen is left with the corn, she will eat it. If the hen is left with the fox, the fox will eat the hen. How can the farmer get all the three things across the river? The farmer takes the hen with him in the boat and leaves it on the other bank. Then he goes back and brings the fox back with him. He drops off the fox on the other side but then brings the hen back along with him. Then he drops it on the first bank and takes the corn with him. He leaves the corn across the river with the fox. Last, he then returns for the last time to get the hen.
  • How far can a fox run into the woods? Halfway; otherwise, he’d be running out of the woods.

Do you have more hard riddles for teens that we missed? Add them to the comments so we can try and solve them!

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