75 Best Confusing Riddles That Make You Scratch Your Head

Last Updated on March 17, 2023 by Michele Tripple

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What starts with T, ends with T, and has T inside? A teapot! For a good brain boost, look no further than these confusing riddles to see if you can solve them. There are some real head-scratchers! 

white emoji face with a confused look and with a question mark on blue background with white text "confusing riddles"

Riddles are a great way to shake off the doldrums and get your brain wheels turning. Every correct answer will build confidence and make you feel like a smart cookie! Grab your family and friends and puzzle your way through these Sphinx-level riddles. Don’t forget to have fun! 
For more brain-tingling riddles, check out Math Riddles and Logic Riddles.

white emoji face with a confused look and with a question mark on pink background with white text "confusing riddles"

Best confusing riddles

Confusing riddle with blue face and red border

Q: I do not have locks, but I have keys. I have no room, but I have space. You cannot go outside, but you can enter.

What am I?

A: A keyboard.

Q: What do you usually get once in a minute, twice in a moment but never comes in a thousand years?

A: The letter ‘M’.

Q: Which dictionary word is misspelled?

A: The word ‘incorrectly.’

Q: What is one question that will get different answers at different times and yet would still be correct?

A: “What’s the time?”

Q: Two sons and two fathers go out fishing. They catch one fish each, but they only bring home three fish. Why?

A: They were father, grandfather, and son.
Confusing riddle with purple face and red border

Q: There are three types of stoves: a brick stove, a glass stove and a wood stove but you have only one match with you. Which one would you have to light up first?

A: The match.

Q: What starts with T, finishes with T, but also has T inside?

A: Teapot

Q: I have forests with no trees, cities with no houses, water with no waves.

What am I?

A: Map

Q: Helen, George, and Ellen are having a cup of coffee while Max, Barb, and Dave are having 7up. What is Elizabeth drinking; coffee or soda?

A: Elizabeth is having coffee. (In her name, the letter E appears twice just like in the other coffee drinkers’ names.)

Q: What is something that you get to keep after you give it to someone?

A: Your word.
Confusing riddle with green face and red border

Q: I have no mouth but I always reply when you speak to me.

What am I?

A: An echo.

Q: In one year, how many months have 28 days?

A: All the months.

Q: What can run but never walks and has a mouth?

A: A river.

Q: What has a neck but no head?

A: A shirt.

Q: What has a face and hands, but cannot smile or hold anything?

A: A clock.
Confusing riddle with orange face and red border

Q: What belongs to you, but others tend to use it more?

A: Your name.

Q: What is the only thing in the world that is perfect?

A: The word “perfect.”

Q: What are the only two things cannot have for breakfast?

A: Lunch and dinner.

Q: Which word becomes shorter when 2 letters are added to it?

A: The word “short.”

Q: What is France’s capital?

A: The letter F.
Confusing riddle with blue face and red border

Q: A cowboy rides to town on Monday and stays for three days, then he leaves on Monday. How?

A: Monday is the name of his horse.

Q: What can travel the world but can never leave a corner?

A: A stamp.

Q: What weighs less when it gets bigger?

A: Popcorn.

Q: What can fill up an entire room, but take up zero space?

A: Light.

Q: I can make polar bears turn white and I can even make you weep. I make guys want to pee and girls want to comb out their hair. I can make famous people look silly and normal people look famous. I can make pancakes turn brown and make a glass of champagne bubble. If I am squeezed I will pop and if you look towards me, you will pop too. Can you guess the riddle?

A: No. (The last sentence is “Can you guess the riddle?”)
Confusing riddle with purple face and red border

Q: Mississippi has four S’s and four I’s. Can you spell that without using S or I?

A: T-H-A-T!

Q: There’s a one-story house where everything is yellow. The walls are yellow. The doors are yellow. All the furniture is yellow. The house has yellow beds and yellow couches. What color are the stairs?

A: There are no stairs—it’s a one-story house!

Q: A girl fell off a 20-foot ladder. She wasn’t hurt. How?

A: She fell off the bottom step.

Q: Grandpa went out for a walk and it started to rain. He didn’t bring an umbrella or a hat. His clothes got soaked, but not a hair on his head was wet. How is this possible?

A: Grandpa’s bald!

Q: You’re in a race and you pass the person in second place. What place are you in now?

A: Second place.
Confusing riddle with gree face and red border

Q: What four-letter word can be written forward, backward, or upside down, and can still be read from left to right?


Q: What is at the end of the rainbow?

A: The letter W!

Q: Name three consecutive days without naming any of the seven days of the week.

A: Yesterday, today, and tomorrow.

Q: You are in a dark room with a box of matches. On a table are a candle, an oil lamp, and a log of firewood. What do you light first?

A: The match! Can’t light any of those things without a lit match.

Q: Two people were playing chess. They both won. How is this possible?

A: They were playing two different games, against other opponents.
Confusing riddle with orange face and red border

Q: What word is always spelled wrong?

A: “Wrong.”

Q: Which letter of the alphabet has the most water?

A: The “C.” Now, see if you can solve this tricky “how many letters are in the alphabet” riddle.

Q: What invention lets you look right through a wall?

A: A window!

Q: Where does today come before yesterday?

A: In the dictionary.

Q: Three doctors all say Robert is their brother. Robert says he has no brothers.

Who is lying?

A: No one—the doctors are Robert’s sisters.
Confusing riddle with blue face and red border

Q: What kind of ship has two mates but no captain?

A: A relationship.

Q: A man is holding exactly $5.25, but only has one coin. How is this possible?

A: He has a quarter and a $5 bill.

Q: I called my dog from the opposite side of the river. The dog crossed the river without getting wet, and without using a bridge, a boat, or a raft. How is that possible?

A: The river was frozen.

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

A: Post office.

Q: You can hold me in your left hand but not your right.

What am I?

A: Your right elbow (or hand)!
Confusing riddle with purple face and red border

Q: I go around all the places, cities, towns, and villages, but never come inside.

What am I?

A: A street.

Q: You go at red and stop at green.

What am I?

A: A watermelon.

Q: I have married many times, but have always been single.

Who am I?

A: A priest.

Q: I am higher without a head.

What am I?

A: A pillow.

Q: I have 13 hearts, but no lungs or stomach.

What am I?

A: A deck of cards.
Confusing riddle with green face and red border

Q: I am easy to lift but hard to throw.

What am I?

A: A feather. (A piece of paper or a leaf would certainly qualify too!)

Q: I break, but never fall. And I fall, but never break.

What are we?

A: Day and night.

Q: Bella is outside a shop. She can’t read the signs, but she knows she needs to go in to make a purchase. What store is she at?

A: An eyeglasses store.

Q: Wednesday, Bill and Jim went to a restaurant they ordered and ate their food and stuff like that. Then they paid the bill, but neither Bill nor Jim paid the bill. Who did?

A: Wednesday did!

Q: What are the next three letters in this sequence: O, T, T, F, F, S, S — what comes next?

A: E, N, T. The letters are the first letters of the written numbers: one, two, three, four, five, etc. “Eight, nine, ten” are next.
Confusing riddle with orange face and red border

Q: How can you physically stand behind your father while he is standing behind you?

A: You and your father are standing back-to-back.

Q: What type of cheese is made backward?

A: Edam.

Q: A girl throws a ball as hard as she can. It comes back to her, even though nothing and nobody touches it. How?

A: She throws it straight up in the air!

Q: An electric train is headed east. Where does the smoke go?

A: Electric trains don’t produce any smoke!

Q: What is the one thing everyone can agree is between heaven and earth?

A: The word “and.”
Confusing riddle with blue face and red border

Q: When is “L” greater than “XL”?

A: When you’re using Roman numerals.

Q: How can the number four be half of five?

A: IV, the Roman numeral for four, is “half” (two letters) of the word five.

Q: A man was driving his truck. His lights weren’t on. The moon was not out. There were no streetlights. Up ahead, a woman was crossing the street. Luckily, the truck driver stopped in time — how did he see her?

A: It was daytime!

Q: A horse attached to a 24-foot chain wants an apple that is 26 feet away. He reaches the apple and munches on it no problem — how is that possible?

A: The other end of the chain isn’t attached to anything.

Q: What has a bottom at the top?

A: Your legs.
Confusing riddle with purple face and red border

Q: If you drop a yellow hat in the Red Sea, what does it become?

A: Wet.

Q: What color is the wind?

A: Blew.

Q: What tastes better than it smells?

A: Your tongue.

Q: What can jump higher than a building?

A: Anything that can jump—buildings can’t jump!

Q: Which word becomes shorter when you add 2 letters to it?

A: “Short.”
Confusing riddle with green face and red border

Q: What has four wheels and flies?

A: A garbage truck.

Q: A monkey, a squirrel, and a bird are racing to the top of a coconut tree. Who will get the banana first?

A: None of them — coconut trees don’t produce bananas!

Q: I can be cracked, I can be made. I can be told, I can be played.

What am I?

A: A joke.

Q: We hurt without moving. We poison without touching. We bear the truth and the lies. We are not to be judged by our size.

What are we?

A: Words.

Q: I am something, I am endless as chain. Once you have me you are bound for life but young girls want me.

What am I?

A: Wedding ring.

Do you have some confusing riddles that make you scratch your head? Share them in the comments to see if we can solve them!

You can Never Have Too Many Riddles! Complete List of Mind-Blowing Riddles!

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