Riddles are a fun and engaging way to stretch your thinking and enhance problem-solving skills. Some riddles are straightforward, but others—like a “hard riddle about a tape measure”—require you to think creatively and look at things from a different angle. These types of puzzles challenge the mind, often involving lateral thinking or wordplay that makes them harder to solve.
In this post, we’ll explore 33 difficult and intriguing riddles, including one centered around a tape measure. Get ready to push your mental limits as we dive into these complex and clever challenges!

All Riddles
1. Riddle:
A hard riddle about a tape measure: I stretch long but can never reach my full length. What am I?
Answer and Explanation
- Answer: A tape measure.
- Explanation: A tape measure stretches to measure things, but it never reaches its “full length” since it’s designed to extend and retract based on the need, always able to pull out more. This riddle uses the metaphor of “full length” in a tricky way.
2. Riddle:
What comes once in a minute, twice in a moment, but never in a thousand years?
Answer and Explanation
- Answer: The letter “M.”
- Explanation: This riddle cleverly uses the letter “M,” which appears once in “minute,” twice in “moment,” and not at all in “a thousand years.”
3. Riddle:
I have a head, a tail, but no body. What am I?
Answer and Explanation
- Answer: A coin.
- Explanation: A coin has a “head” side and a “tail” side, but it doesn’t have a body, which makes this riddle an easy-to-solve classic.
4. Riddle:
The more you take, the more you leave behind. What am I?
Answer and Explanation
- Answer: Footsteps.
- Explanation: Footsteps are left behind as you walk, and the more steps you take, the more you leave behind, which makes this a clever riddle.
5. Riddle:
What has many keys but can’t open a single lock?
Answer and Explanation
- Answer: A piano.
- Explanation: A piano has many keys, but these are for playing music, not for opening locks, making this a great riddle that plays with the different meanings of the word “key.”
6. Riddle:
I can be cracked, made, told, and played. What am I?
Answer and Explanation
- Answer: A joke.
- Explanation: A joke can be cracked (as in telling a joke), made, told to others, or played on someone, adding a fun twist to the riddle.
7. Riddle:
What can travel around the world while staying in the corner?
Answer and Explanation
- Answer: A stamp.
- Explanation: A stamp is placed in the corner of an envelope, which can then travel around the world, making it a perfect riddle for those who like wordplay.
8. Riddle:
I speak without a mouth and hear without ears. I have no body, but I come alive with the wind. What am I?
Answer and Explanation
- Answer: An echo.
- Explanation: An echo repeats sound, without having a mouth or ears, and comes alive in places where sound travels.
9. Riddle:
What can be broken but never held?
Answer and Explanation
- Answer: A promise.
- Explanation: A promise can be broken, but it isn’t something that can physically be held, making it a great abstract riddle.
10. Riddle:
I am taken from a mine, and shut up in a wooden case, from which I am never released, and yet I am used by almost every person. What am I?
Answer and Explanation
- Answer: Pencil lead (graphite).
- Explanation: Graphite is mined, encased in wood to make a pencil, and used by people every day for writing.
11. Riddle:
What can fill a room but takes up no space?
Answer and Explanation
- Answer: Light.
- Explanation: Light can fill a room by illuminating it, but it takes up no physical space, which makes it an interesting riddle.
12. Riddle:
What is black when you buy it, red when you use it, and gray when you throw it away?
Answer and Explanation
- Answer: Charcoal.
- Explanation: Charcoal is black when purchased, turns red when it burns, and becomes gray when it is used up, making it an easy riddle with a fun twist.
13. Riddle:
What has a neck but no head?
Answer and Explanation
- Answer: A bottle.
- Explanation: A bottle has a neck, but it doesn’t have a head, offering a simple but tricky riddle.
14. Riddle:
What gets wetter as it dries?
Answer and Explanation
- Answer: A towel.
- Explanation: A towel dries something off, but as it absorbs moisture, it gets wetter, making it a fun riddle to solve.
15. Riddle:
I have a spine but no bones. What am I?
Answer and Explanation
- Answer: A book.
- Explanation: A book has a spine (the part that holds the pages together), but it doesn’t have bones, which makes this a clever wordplay riddle.
16. Riddle:
What has one eye but cannot see?
Answer and Explanation
- Answer: A needle.
- Explanation: A needle has an eye (the hole for the thread), but it cannot see, creating an interesting and challenging riddle.
17. Riddle:
I am always in front of you but can’t be seen. What am I?
Answer and Explanation
- Answer: The future.
- Explanation: The future is always ahead of us, but it remains invisible and unknown until it arrives, which makes it a philosophical riddle.
18. Riddle:
What can be written, but never seen?
Answer and Explanation
- Answer: A thought.
- Explanation: A thought can be written down, but it can’t be physically seen by others, making this a deep riddle to ponder.
19. Riddle:
I have many teeth but don’t bite. What am I?
Answer and Explanation
- Answer: A comb.
- Explanation: A comb has many “teeth,” but they don’t bite, making this a playful and simple riddle.
20. Riddle:
What can be cracked, made, told, and played?
Answer and Explanation
- Answer: A joke.
- Explanation: A joke can be cracked (as in telling a joke), made, told to others, or played on someone, offering a fun challenge to solve.
21. Riddle:
What is always coming but never arrives?
Answer and Explanation
- Answer: Tomorrow.
- Explanation: Tomorrow is always coming, but it never arrives, making this a timeless and philosophical riddle.
22. Riddle:
What has a thumb and four fingers but isn’t alive?
Answer and Explanation
- Answer: A glove.
- Explanation: A glove has a thumb and four fingers but isn’t alive, which makes it a fun riddle to solve.
23. Riddle:
What can be caught but not thrown?
Answer and Explanation
- Answer: A cold.
- Explanation: A cold is something you can “catch,” but you can’t physically throw it, making this a light-hearted riddle.
24. Riddle:
What has a head, a tail, but no body?
Answer and Explanation
- Answer: A coin.
- Explanation: A coin has two sides, commonly referred to as “head” and “tail,” but it lacks a body, making it an easy-to-understand but tricky riddle.
25. Riddle:
I am full of holes, but I can still hold a lot of weight. What am I?
Answer and Explanation
- Answer: A net.
- Explanation: A net is full of holes but can still hold things, such as when used to carry items or catch fish.
26. Riddle:
I am always in front of you but can’t be seen. What am I?
Answer and Explanation
- Answer: The future.
- Explanation: The future is always ahead of us but is invisible and can’t be seen, offering a tricky and thought-provoking riddle.
27. Riddle:
What has keys but can’t open locks?
Answer and Explanation
- Answer: A piano.
- Explanation: A piano has keys that create music, but they cannot open locks, making this a clever wordplay riddle.
28. Riddle:
What can be broken, even if you never pick it up or touch it?
Answer and Explanation
- Answer: A promise.
- Explanation: A promise can be broken through actions or words, even though it’s not a physical object.
29. Riddle:
What has one eye but can’t see?
Answer and Explanation
- Answer: A needle.
- Explanation: A needle has an eye (the hole for the thread), but it cannot see, offering a fun riddle based on wordplay.
30. Riddle:
What has a spine but no bones?
Answer and Explanation
- Answer: A book.
- Explanation: A book has a spine (the part that holds the pages together), but it doesn’t have any bones, making this an easy riddle to understand.
31. Riddle:
What has a head, a tail, but no body?
Answer and Explanation
- Answer: A coin.
- Explanation: A coin has a head and a tail, but no body, which makes it a simple yet tricky riddle.
32. Riddle:
What gets wetter the more it dries?
Answer and Explanation
- Answer: A towel.
- Explanation: A towel dries things off, but as it does, it becomes wetter, making this a clever and easy-to-solve riddle.
33. Riddle:
What has keys but doesn’t open locks?
Answer and Explanation
- Answer: A piano.
- Explanation: A piano has keys, but they are used for making music, not for opening locks, making this a fun riddle to solve.
Conclusion
Hard riddles like the one about a tape measure challenge us to think creatively and use our problem-solving skills in new ways. The satisfaction that comes from solving these tricky puzzles is unmatched, and they offer a great way to exercise the brain. Whether you’re a beginner or an experienced riddle solver, there’s always room for a fun challenge.
Do you have any favorite hard riddles? Share them with us in the comments below! We’d love to see if you can stump us with your most challenging puzzles!