The 50 Very Best Riddles for Teens

Most parents of teenagers feel like they have a stranger living in their house. The child who followed you around, constantly begging for your attention, would now rather have nothing to do with you and would prefer if you just left them alone. Trying to get them to laugh and lighten up isn’t as easy as it used to be. But teenagers never back down from a challenge with their “know-it-all” attitudes, so connect with them by asking them to crack these riddles.

1. Riddle: What Will You Open First?

You stay alone and you’re sleeping in your room when your friends are ringing the doorbell. They’ve come to have breakfast with you and all you have at home is a box of cornflakes, bread, jam, and one carton of milk. What will you open first?

Your teen will think you’re trying to trick them with any riddle you tell them. They will probably ignore the list of food items you listed, and answer “the door.” After all, your friends can’t come in and eat with you if you don’t open the door for them to come inside. But nope, that’s not quite right. Before you can even let them in, you have to wake up and waking up means opening. . . 

Answer: Your eyes

2. Riddle: What Cannot Talk but Will Always Reply?

What cannot talk but will always reply when spoken to?

Your teen may try to challenge you on this one, and give reasons why answers like “a parrot, Siri, or Alexa” could be right. And while they may be wrong, hear them out because they are using reasoning skills to argue their point!

Answer: An echo

3. Riddle: The Rhyme of What Am I?

I begin like a groan hollowed out with ease, then end like a mouse with a head of hard cheese. What am I?

This one is sure to stump your teen. It might make more sense to them once they hear the answer. If your teen gets it right the first time, they’ve either heard the riddle before or are well on their way to earning a college scholarship. 

Answer: A greenhouse

4. Riddle: It Doesn’t Move. Or Does It?

What goes up and down but doesn’t move?

Your teen’s first thought may be “age.” And while we wish our age could go down, it can’t. This object can indeed go up and down without moving an inch. 

Answer: Stairs

5. Riddle: Your Mother’s Brother’s Brother-In-Law

Your mother’s brother’s only brother-in-law is asleep on your bed. Who is asleep on your bed?

This riddle isn’t as tricky as it sounds. The challenge is trying to keep track of the people mentioned and deciphering their relationship with one another. The keyword in this riddle that gives away the answer is “only.” If your mother’s brother (your uncle) only has one brother-in-law then that means the person sleeping on your bed is married to your mom. 

Answer: Your father

6. Riddle: What Can Fill a Room?

What can fill a room but takes up no space?

This riddle is a tricky one! Most teens will try to think of a physical, tangible object that could fill a room but take up little space. But the kicker here is that the answer takes up NO space. Therefore, it must be something that’s intangible. What’s ironic is that your teen is really good at giving you this type of “treatment” when they’re grounded. 

Answer: Silence

7. Riddle: Useless Unless Broken 

What has to be broken before it can be used?

This riddle seems so simple, but how many things need to be physically broken before they can actually be used? We only know of one and it’s the answer to this riddle. If your teen likes to cook or help you around the kitchen, they might get this one right. But if your teen is like most and doesn’t want to lend a helping hand, they may be trying to figure this out for a while. 

Answer: An egg

8. Riddle: What Never Arrives?

What is always coming, but never arrives?

If your teen is having a bad day, you might try to cheer them up by telling them today will end and tomorrow will come. Tomorrow will come, but when it arrives, it never arrives as tomorrow. It arrives as today. And that’s why this riddle is so tricky!

Answer: Tomorrow

9. Riddle: The Forwards and Backwards Riddle

Forward I’m heavy. Backwards I’m not. What am I?

We’ll give you a hint for this one, and you can decide if your teen deserves to hear it too. The answer is written in the riddle. Whether it’s written forwards or backwards though, we can’t say. 

Answer: Ton

10. Riddle: Think Outside the Room

What kind of room has no doors or windows?

Even we couldn’t guess the answer to this riddle, so we’re betting it will keep your teen guessing for hours too. 

Answer: A mushroom

11. Riddle: Know Your Trees

What kind of tree can you carry in your hand?

You don’t really have to know different types of trees to get the answer to this right. Think about what your hand and a certain type of tree may have in common. 

Answer: A palm

12. Riddle: Running in Place

If you’re running in a race and you pass the person in second place, what place are you in?

Riddles are all about word choice and word order. Paying special attention to each word in a riddle is the key to figuring out the right answer. Your teen will automatically assume that passing the person in second means you’ll be in first. But you didn’t pass the person in first place so that’s not possible.

Answer: Second place

13. Riddle: Got to Hand It to You

What has a thumb but no fingers and is not living?

It’s impossible to think of something that has only a thumb and is not alive. But just as some riddles rely on precise wording to trick people, other riddles rely on leaving information out. Technically, a mitten doesn’t have a thumb or fingers. It has a spot for a thumb and a spot for all the fingers together. 

Answer: A mitten

14. Riddle: Who Paid the Bill?

Tuesday, Sam and Peter went to a restaurant to eat lunch. After eating lunch, only one of them paid the bill. But Sam and Peter did not pay the bill, so who did?

Your teen’s initial thought will be someone who isn’t named in the riddle. Maybe their waiter took care of the bill for them? Maybe it was on the house? Or maybe, your teen will realize that it’s not uncommon for a person to be named after a day of the week. 

Answer: Their friend, Tuesday

15. Riddle: What Comes Next?

What is next in this sequence? JFMAMJJASON. . . 

Teens are used to figuring out sequences and patterns when it comes to standardized tests. They will try to make sense of these letters put together. There are three “J” letters. There’s the name Jason spelled out at the end. What could possibly come next? Well, once your teen realizes that the sequence contains the first letter of each month, it shouldn’t be too hard. 

Answer: The letter “D”

16. Riddle: Got Any Sleep?

During which month do people sleep the least?

When teens try to answer this riddle, they start immediately reasoning. Which month would be so stressful and busy that it would cause people to lose sleep? And while we could speculate it’s December when everyone’s busy shopping and staying up to catch a glimpse of Santa, the answer to this is a little more literal. 

Answer: February (there are literally fewer nights in February)

17. Riddle: Letter Me This

What happens four times in a teenager’s life, once in adult life and never in childhood?

Here we go again with the “literal” riddles. We hope you and your teen enjoy them as much as we do. 

Answer: The letter E

18. Riddle: Choo-Choo 

If an electric train is traveling south, which way is the smoke blowing?

Does your teen know much about trains? Or about wind patterns and directions? We’re guessing not. This one will sure make them feel silly about thinking so hard once they hear the answer. 

Answer: There is no smoke because it’s an electric train

19. Riddle: Family Math 

Two fathers and two sons went duck hunting. Each shot a duck but they shot only three ducks in all. How come?

Even if math isn’t your teen’s best subject, they will know the math in this riddle doesn’t seem to add up. If we add two and two like the riddle mentions, then of course we get four people, which would mean four ducks shot in total if everyone shot a duck. BUT. If you realize that two people on the trip are fathers, and two are sons. You realize you can have one person who is both a father and a son. 

Answer: The hunters were a man, his son, and his grandson.

20. Riddle: Guess the Weight 

Paul’s height is six feet, he’s an assistant at a butcher’s shop, and wears size 9 shoes. What does he weigh?

We can do our best to try and guesstimate Paul’s weight, but the riddle doesn’t want us to do that. Instead, the riddle wants us to realize that it gave us a hint already. 

Answer: Meat

21. Riddle: Cheer Up Buttercup

What fruit is always sad?

We’re not sure how to tell if a fruit is sad or not. Your teen will wonder this too. 

Answer: A blueberry

22. Riddle: No Mouth or Legs 

What has a mouth but cannot eat and runs but has no legs?

Some riddles paint a picture of creatures that seem scary and most definitely don’t exist. If you’re teen knows their geography terms or types of waterways, this one shouldn’t make them picture anything too scary. 

Answer: A river

23. Riddle: Down on the Farm 

A farmer is walking towards his field. On the way, he sees three frogs sitting on the shoulders of two rabbits. Three parrots and four mice run towards him. How many pairs of legs are going towards the field?

We’re betting your teen will bust out pen and paper to keep track of all the animals and then to count up how many legs there are. Try not to laugh too much. It’s an honest mistake. 

Answer: Only two – the farmer’s

24. Riddle: The Invincible Riddle 

The person who buys me cannot use me, and the person who uses me cannot buy me or see me. What am I?

This riddle is a doozy. It will keep your teen thinking in circles. 

Answer: A coffin

25. Riddle: Count the Apples 

If there are 6 apples in a bowl and you take away two of them. How many apples will you have?

Keep in mind that the riddle is not asking how many apples are left in the bowl. 

Answer: Two apples

26. Riddle: No Survivors 

When a train derailed and crashed, every single person in it died. Who survived?

The word “single” can have multiple meanings. Though the riddle will make your teen think that there were no survivors in the train wreck, it’s not true. 

Answer: Everyone who was not single at the time.

27. Riddle: The Umbrella Conundrum

A group of five friends went out for a field trip. They had to share one umbrella with their pets. Surprisingly no one got wet. How come?

Either this umbrella is a magic shield or larger than life to be able to protect this many from getting wet. Have your teens sharpen their critical thinking skills by asking what the weather was like on this field trip. 

Answer: It never rained.

28. Riddle: What’s for Dinner?

Families and individuals buy me to eat but no one ends up eating me. What am I?

What would you buy to eat but not end up ever eating? Maybe it’s not something you help, but something to help you eat. 

Answer: Utensil

29. Riddle: A Frying Pan 

Why do people believe Europe is like a frying pan?

Your teen doesn’t need to have traveled to Europe to be able to figure this riddle out. But they may need to know a bit of Europe’s geography. Have them look at a map. 

Answer: It has Greece at the bottom of it.

30. Riddle: An Easy In 

What is so easy to get into but very hard to get out?

Every teen should know the answer to this riddle because teens are notorious for getting into this. 

Answer: Trouble

31. Riddle: A Number In Between 

What do you add between the numbers 3 and 4 to get a number greater than three but less than four?

Riddles containing math are some of the easiest ways to trick your teens. 

Answer: Add a decimal to get 3.4

32. Riddle: Mr. Bunny’s Children 

Mr. Bunny has three daughters and each of them has one brother. How many kids are there in Mr. Bunny’s family?

Bunny parents have more children than any other type of animals. Your teen may think the answer to this riddle is a high number. But the answer requires only simple math. 

Answer: Four kids

33. Riddle: More Broken Eggs 

A girl buys a dozen eggs and, on the way home, all but seven break. How many eggs are left unbroken?

That pesky word “all” is used in this riddle to throw everyone off the course to the right answer. It makes us think that seven break, but it’s five that break. Your teen may refuse to eat eggs ever again with all these egg riddles. 

Answer: Seven

34. Riddle: Guess the Ball 

I am a ball that rolls but can’t bounce or be thrown. What am I?

Your teen may argue that a bowling ball is the correct answer. And while we agree that a bowling ball shouldn’t be thrown, it is sorta kinda thrown when people roll it down the lane. 

Answer: An eyeball

35. Riddle: Fox on the Run 

How far can a fox run into the woods?

This riddle might make your teen roll their eyes, but that’s ok because what doesn’t make them roll their eyes these days? However, we all know that they will be silently thinking how clever this riddle is and how clever you are as a parent. Right? 

Answer: Halfway; otherwise, he would be running out of the woods.

36. Riddle: Guess the Child’s Name

Greg’s mother had three children. The first child was named April. The second child was named May. What was the third child’s name?

This riddle is a great example of how tricksters often use preconceived ideas against you. Even though the answer is right in front of you, you can’t help but overthink. 

Answer: Greg

37. Riddle: Futuristic Car

What has four wheels and flies? 

This riddle is a clever stumper. Outside of sci-fi movies, no vehicle can fly yet. The term “flies” refers to the insect and not the action of flying. 

Answer: A garbage truck

38. Riddle: The Twins Riddle 

Two children are born on the same day by the same mother, but they are not twins. How is that possible? 

Since the riddle implies that the children are not twins, the only logical explanation is that the children are part of a more significant multiple birth. 

Answer: They are part of triplets

39. Riddle: Which Direction?

A group of students was standing in the blazing sun facing due west on a march past event. The leader shouted at them: Right turn! About turn! Left turn! At the end of these commands, which direction are the students facing now?

If your teen can keep up with this riddle, they will realize that a right turn makes the group face North. An about-turn is a 180-degree spin, and then the left turn will make the group face their final direction. 

Answer: East

40. Riddle: Permanent Shoes 

What always goes to sleep with shoes on?

This riddle may be a bit silly, but we guarantee it will keep your teen thinking for a little while. 

Answer: A horse

41. Riddle: Spellcheck 

One word in the dictionary is spelled wrong. What is it?

The only word in the English language spelled wrong in the dictionary is literally the word “wrong.” See what we did there?

Answer: Wrong

42. Riddle: Saving Money at the Movies

If you go to the movies and you’re paying, is it cheaper to take one friend to the movies twice or two friends to the movies at the same time?

This one will really make you think for a minute. If you take one friend to the movies twice, you’ll be buying four tickets total because you have to buy yourself a ticket two times. But you’d only be buying three tickets if you took two friends at the same time. 

Answer: Two friends at the same time

43. Riddle: How Many Bananas?

How many bananas can you eat if your stomach is empty?

Your teen will think about how many bananas the average person can eat in one sitting. The phrase “your stomach is empty” throws people off. Once you eat one banana, your stomach is no longer empty. 

Answer: One

44. Riddle: World Traveler 

What can travel around the world while staying in a corner?

Lots of things travel around the world, but what stays in a corner? And what kind of corner are we talking about? Your teen may spend time trying to figure out what kind of corner the riddle could be referring to. 

Answer: A stamp

45. Riddle: Lucky Number 7

How do you make the number 7 an even number without addition, subtraction, multiplication, or division? 

This is a tricky one! Leave it to riddlers to use our poor math skills against us. 

Answer: Drop the “S”

46. Answer: One Side of the River

A man stands on one side of a river, his dog on the other. The man calls his dog, who immediately crosses the river without getting wet and without using a bridge or a boat. How did the dog do it?

We’re used to hearing jokes about why the chicken crossed the road, but this riddle takes things up a notch with a dog and a river. 

Answer: The river was frozen.

47. Riddle: Buried Alive 

You bury me when I am alive, and dig me up when I die. What am I?

We love the “what am I” riddles and think your teen will too. 

Answer: A plant

48. Riddle: Runs Forever 

This old one runs forever, but never moves at all. He has no lungs nor throat, but still a mighty roaring call. What is it?

This riddle uses the word “he” to throw your guess off. Your teen will automatically assume this “he” is a person or something alive that is male. But the answer is neither!

Answer: A waterfall

49. Riddle: Missed and Measured 

Until I am measured, I am not known. Yet how you miss me when I have flown. 

Despite “time” controlling all aspects of our lives, we often forget time is a manmade construct. Time only exists because humans created it. Yet, we can’t imagine a world without it. 

Answer: Time

50. Riddle: Wiggle Worm 

What is a worm that does not wiggle?

If your teen spends a lot of time with their head in books or in the library, perhaps they will answer this riddle easily!

Answer: A bookworm

Here are some extra riddles for fun!

51. Riddle: Can’t Go in the Pot 

What can never be put in a saucepan? 

Answer: Its lid.

52. Riddle: Word Math

What two words, added together, contain the most letters? 

Answer: Post office

53. Riddle: 8 Eights 

Can you write down eight eights so that they add up to one thousand?

Answer: 888 + 88 + 8 + 8 + 8 = 1,000

54. Riddle: The Age Riddle

When asked how old she was, Suzie replied, “In two years I will be twice as old as I was five years ago.” How old is she?

Answer: She’s 12

55. Riddle: John’s Height 

When John was 6 years old, he hammered a nail into his favorite tree to mark his height. Ten years later, at age 16, John returned to see how much higher the nail was. If the tree grew by 5 centimeters each year, how much higher would the nail be?

Answer: The nail would be at the same height since trees grow at their tops. 

More Riddles

55 Riddles for Teens // 136 Riddles for Adults // 55 Animal Riddles
75 Short Riddles // 40 Emoji Riddles // 172 Riddles for Kids
154 Trick Questions // 154 Funny Riddles // 73 Brain Teasers
82 Hard Riddles // 73 Dirty Riddles // 73 What Am I Riddles // 37 Egg Riddles