How good is your riddle game? Would you consider yourself a riddle novice or a riddle ninja?

Riddles are an easy way to keep the creative juices flowing. They even make our brains function differently! They can be a mental workout, for sure, but if you’re a seasoned master, most riddles probably don’t challenge you enough. If you’re looking to up the ante, our collection of tough riddles should do the trick. We’ve searched and have found 40 really hard riddles for you to put your solving skills to the test!

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Test Your Trivia Knowledge

If you love quirky questions and guessing games, we have just the thing for your next night in. Virtual Game Night from Let’s Roam will have you and up to 15 of your fellow thinkers testing your brainpower! There are tons of options; categories include sports, animals, TV, geography, movies, pop culture, politics, cartoons, and more. It’s all waiting for you in our easy-to-use video interface so, when you’ve finished solving all of the really hard riddles, be sure to sign up for 7 days of free fun!

1. Riddle: What is there one of in every corner and two of in every room? Answer: The letter O.

2. Riddle: What is stronger than steel but can’t handle the sun? Answer: Ice.

3. Riddle: What is it that no one wants, but no one wants to lose? Answer: A lawsuit.

4. Riddle: The more there is, the less you see. What am I?Answer: Darkness.

5. Riddle: How do eight eights add up to one thousand? Answer: 888 + 88 + 8 + 8 + 8 = 1000.

6. Riddle: I have many faces, expressions, and emotions, and I am usually right at your fingertips. What am I?Answer: Emojis.

7. Riddle: I’m full of holes but strong as steel. What am I?Answer: A chain.

8. Riddle: A barrel of water weighed 60 pounds. Someone put something in it and now it weighs 40 pounds. What did the person add?Answer: A hole.

9. Riddle: You are my brother, but I am not your brother. Who am I? Answer: I am your sister.

10. Riddle: If all Wibbles are Criggles, all Borkins are Kwumblins, no Hoggles are Borkins, and all Criggles are Borkins, is it true that all Borkins are Criggles? Answer: Nope.

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Are these really making you think? Give your mind a rest with some funny riddles!

11. Riddle: What word has kst in the middle, in the beginning, and at the end? Answer: Inkstand

12. Riddle: What bird do you associate with lifting weight? Answer: A crane.

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13. Riddle: Two men are in a desert. They both have backpacks on. One of the guys is dead. The guy who is alive has his backpack open and the guy who is dead has his backpack closed. What is in the dead man’s backpack? Answer: A parachute.

14. Riddle: What walks on four feet in the morning, two in the afternoon, and three at night? Answer: A man. The times of day represent a lifetime. He crawls as a baby, walks as an adult, and walks with a cane as an elder man.

15. Riddle: One day, a magician was boasting about how long he could hold his breath underwater. His record was 6 minutes. A kid that was listening said, “that’s nothing, I can stay underwater for 10 minutes using no equipment or air pockets!” The magician told the kid if he could do that, he’d give him $10,000. The kid did it and won the money. How? Answer: He filled a glass of water and held it above his head for 10 minutes.

16. Riddle: What is it that given one, you’ll have either two or none? Answer: A choice.

17. Riddle: I can be long or can be short, I can be black, white, brown, or purple. You can find me the world over and I am often the main feature. What am I? Answer: Rice.

18. Riddle: How can the number four be half of five? Answer: IV, the Roman numeral for four, is half (two letters) of the word five.

19. Riddle: I am something people celebrate or resist. I change people’s thoughts and lives. I am obvious to some people but, to others, I am a mystery. What am I? Answer: Age.

20. Riddle: Nobody has ever walked this way. Which way is it?Answer: The Milky Way.

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If these really hard riddles are too tough, try these easy riddles!

21. Riddle: It can’t be touched and can’t be felt. It can’t be seen, or heard, or smelt. It lies behind stars and under hills, and any empty holes it fills. It comes early and follows after, ends life, and kills laughter. What is it? Answer: Darkness.

22. Riddle: What grows up while growing down? Answer: A goose or duck.

23. Riddle: A man runs away from home. He turns left but keeps running. After some time, he turns left again and keeps running. He later turns left once more and runs back home. Who was the man in the mask? Answer: A baseball player running the bases.

24. Riddle: Sometimes narrow, sometimes wide, wind or rain, I stay outside. Even if there’s heat or snow, from house to house I will still go. What am I? Answer: A path.

25. Riddle: I have three feet, but I can’t stand without leaning. I have no arms to hold me up. What am I? Answer: A yardstick.

26. Riddle: What can go through glass without breaking it? Answer: Light.

27. Riddle: It’s shorter than the rest, but when you’re satisfied, you bring it up. What is it? Answer: Your thumb.

28. Riddle: I speak without a mouth and hear without ears. I’m invisible, but you can call for me. What am I?Answer: An echo.

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29. Riddle: What has ten letters and starts with gas? Answer: An automobile

30. Riddle: What connects two people, but touches only one? Answer: A wedding ring

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When you’re tired of really hard riddles, see how children answer these riddles for kids!

31. Riddle: They can be harbored, but few hold water. You can nurse them, but only by holding them against someone else. You can carry them, but not with your arms. You can bury them, but not in the earth. Answer: Grudges.

32. Riddle: What has a neck but no head, two arms, and no hands? Answer: A shirt.

33. Riddle: I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I? Answer: A map.

34. Riddle: A woman shoots her husband, then holds him underwater for five minutes. Next, she hangs him. Afterward, they enjoy a lovely dinner. How? Answer: She took a picture of him and developed it in her darkroom.

35. Riddle: I only lie down once in my life—when I die. What am I?Answer: A tree.

36. Riddle: Who can finish a book without finishing a sentence?Answer: A prisoner.

37. Riddle: What ancient invention allows people to see through walls?Answer: Windows.

38. Riddle: One knight, a ninja, and a pirate were on a ship. The ship began to sink. The ninja and the pirate jumped into a lifeboat before the ship went underwater. Who died?Answer: The knight.

39. Riddle: What has ten letters and starts with gas?Answer: Automobile.

40. Riddle: A man drove from New York City to Los Angeles in four days. At the end of his trip, he discovered that one of his tires had been punctured. How was he able to make the drive?Answer: It was his spare tire.

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Which riddle stumped you the most? Have any really hard riddles of your own? Let us know in the comments!

If you haven’t had enough brain teasers, try our ultimate list of 150 riddles!

Ready for Some Fun with Friends?

Keep your thinking cap on, gather your group, and get your free trial of Let’s Roam’s Virtual Game Night! You’ll get 7 days of unlimited trivia, challenges, drawing games, emoji decoders, and more! Invite 15 friends or family members and choose from over 15 fun-filled options. If you love it (and we’re sure you will!) you and yours can make game nights a regular thing! What are you waiting for?

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