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What Are Riddles?

A riddle is like a puzzle for your brain. It can come as a statement, question, or phrase with a double meaning and requires unexpected or clever answers.

The answers to tricky riddles can either stump you until you can’t sleep thinking about it, or they can be surprisingly simple that it will make you go, “Why didn’t I think of that?!”

Riddles are meant to be fun puzzles for everyone to enjoy. Solving riddles is already fun when you’re on your own, but it’s even more entertaining watching your friends’ expressions as they try to figure out the answers!

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👉 While you can use these riddles as icebreakers, there are other ways of making people laugh. Strike up any conversation with this list of conversation starters!

Really Hard Riddles

Want to take your riddles up a notch? Look no further because we’ve put together a list of really hard riddles that will put anyone’s critical thinking skills and street smarts to the test!

These riddles are both challenging and fun and will force you to think outside the box.

How many of these tough riddles can you answer?

1. What bird can lift heavyweights?

Answer: A crane. It’s a bird AND a machine!

2. What is found in every corner and two in every room?

Answer: The letter O. Get it?

3. I’m delicious and give lots of energy. I’m a fruit, but you can also see me on the calendar. What am I?

Answer: Date. Yummy calendars!

4. What is it that given one, you’ll have either two or more, or none at all?

Answer: A choice. I hate it when I have no choice on the matter.

5. I’m full of holes but strong as steel. What am I?

Answer: A chain. Holes don’t always mean fragile!

6. What has an eye but cannot see?

Answer: A needle. It can’t see, but it sure can sew.

7. How can the number four behalf of five?

Answer: The letters I and V are half of the letters in the word FIVE.

8. Nobody has ever walked this way. Which way is it?

Answer: The Milky Way. Sounds delicious.

9. What belongs to you, but everyone else can use it?

Answer: Your name. Better than people calling you “hey, you” all the time.

10. What has a face and two hands but no arms or legs?

Answer: A clock. They wave at me all the time.

Super Hard Riddles

These super hard riddles will make you and your friends question your intelligence. They’re so hard to answer that you’ll need to take a minute or two or more for you to figure it out!

Don’t worry if you can’t answer them. Chances are some of your friends won’t be able to answer them too! What’s important is that everyone has a good time while racking their brains for answers!

1. What English word has three consecutive double letters?

Answer: Bookkeeper. He must like books.

2. What can go up a chimney when down but unable to go up a chimney when up?

Answer: An umbrella. Mary Poppins would enjoy this one.

3. How is seven different from the rest of the numbers between one and ten?

Answer: Seven has two syllables, and the other numbers only have one syllable.

4. What disappears as soon as you say its name?

Answer: Silence. This one is a thinker.

5. What does no one want, but they don’t want to lose?

Answer: A lawsuit. No one would want to lose that.

6. It comes once in a minute, twice in a moment, but never in a thousand years?

Answer: The letter M. Think outside of the box!

7. People in poverty have this. If you eat this, you will die. What is it?

Answer: Nothing. The harsh realities of life.

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8. First, you eat me. Then you get eaten. What am I?

Answer: A fish hook. For the fish out there.

9. What are the next three letters in this combination:

Answer: OTTFFSS? E N T. (Eight, nine, ten)

10. The more there is, the less you see. What am I?

Answer: Darkness. Without light, there is only darkness.

Funny Hard Riddles

While riddles are brain teasers that will consume most of your brainpower, they can also be fun mysteries that can bring people together. You’d be surprised at how a healthy competition on who can get the most right answers to riddles can be so hilarious and entertaining!

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Good thing we’ve put together a list of the best funny hard riddles that will ask you questions about anything under the sun while making you laugh too!

1. I have many faces, expressions, and emotions, and I am usually right at your fingertips. What am I?

Answer: Emojis. I use emojis to express my emotions for the day.

2. What two things can you never eat for breakfast?

Answer: Lunch and Dinner. But of course!

3. What is orange and sounds like a parrot?

Answer: A Carrot. They’re both cute too.

🤓 Suggested read: 45+ 'What Do You Call?' Jokes To Make Your Friends Laugh

4. Which word in the dictionary is always spelled incorrectly?

Answer: Incorrectly. The answer was right there!

5. What do Alexander The Great and Winnie The Pooh have in common?

Answer: Same middle name. Duh also rhymes with The.

6. It’s shorter than the rest, but when you’re satisfied, you bring it up. What is it?

Answer: Your thumb. Thumbs up for this riddle.

7. You are my brother, but I am not your brother. Who am I?

Answer: I am your sister. Now this is just silly.

8. How many letters are in the alphabet?

Answer: 11 letters. If your answer was 26, you forgot this was a riddle.

9. What has a head and a tail but no body?

Answer: A coin. Oldie but goodie.

10. During what month do people sleep the least?

Answer: February, it’s the shortest month. People are awake the least this month too!

Bonus: Hard Riddles for Adults

For those looking for riddles that kids shouldn’t hear about, we’ve come up with a list of funny hard riddles for adults. Aside from being hard to answer, these riddles can be pretty naughty and dirty, making them perfect for parties or date nights!

Test how dirty-minded you and your friends are with these hard riddles for adults!

1. I go in hard. I come out soft. You blow me hard. What am I?

Answer: Chewing gum. It’s delicious and chewy too.

👉 Suggested read: Funny Questions to Ask - Conversation Starters

2. What 3 letter word starts with S, ends with X and has a vowel in the middle?

Answer: SIX. If your answer was the other word, you have a dirty mind.

3. I saw a boat full of people, but there wasn’t a single person on the boat. Why is that?

Answer: They were all married. The married guy not wearing his ring begs to differ!

4. While I enjoy a soft blow, other times, I need a stronger blow to get all that goop to come out. What am I?

Answer: A nose. Blow it to get all that goop out.

5. What tastes better than it smells?

Answer: A Tongue. Because it can taste, but it can’t smell.

6. What do men have in their pants that women can’t get enough of? Women go crazy about, and love to get their hands on it until it’s fully spent?

Answer: A credit card. Max that card out.

7. The one who makes it doesn’t use it. The one who buys it doesn’t need it. The one who uses it doesn’t know it. What is it?

Answer: A coffin. It makes sense the more you think about it.

8. I am long. You move me around with your lips and tongue. I get wet with saliva and I get sucked. What am I?

Answer: A straw. Sometimes you bite it too!

9. When people think of me, the word “hump” comes to mind. You can find me in a woman’s pants when they’re too tight. What am I?

Answer: Cameltoe. Something women don’t like!

10. I am long and hard, and you will happily spend money on me. After getting me, you feel a huge feeling of relief. What am I?

Answer: An education. Maybe that will help me answer these riddles better next time!

👉 Looking for more riddles to try on your family and friends? Up your conversation game with any of these 400+riddles!

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Conversation Starters

Looking for some conversation starters and icebreakers? Check out our collection of articles full of tips, tricks, and ideas to help get the conversation flowing! Get to know how to talk to anyone anytime, anywhere!