16 Head-Scratching Riddles To Make You Think

Monday, November 13, 2023

Language may drastically change over time, but many of the ways in which we use it have stayed the same, a phenomenon proven by ancient riddles and “yo mama” jokes discovered on Mesopotamian and Babylonian tablets dating back thousands of years. Indeed, it seems probable that for as long as we’ve been communicating with each other, we’ve been finding ways to keep things interesting with wordplay, good-natured razzing, and riddles.

Though linguistic trickery is found in all corners of the globe, the word “riddle” originated from the Common Germanic verb rēdaną, which means “to interpret or guess.” Within the definition lies the explanation for what makes riddles so appealing and hilariously frustrating: There are often many potential answers, but it’s the guesser’s responsibility to outsmart the riddler by choosing the right one.

Riddles are part brainteaser, part joke, and part exploration into the subtle nuances of language. We challenge you to guess the correct answers to these head-scratching riddles, and then scroll down to see whether you’re right.

The Riddles

1. I have cities but no houses; I have mountains but no trees; I have water but no fish. What am I?

2. If you eat me, my sender will eat you. What am I?

3. What living thing has a heart that doesn’t beat?

4. What’s the coolest letter in the alphabet?

5. I can fly but have no wings; I can cry but have no eyes. What am I?

6. Always in you, sometimes on you; if I surround you, I can kill you. What am I?

7. What can’t be burned in a fire nor drowned in water?

8. What word gets shorter when you add two letters to it?

9. A barrel of water weighs 60 pounds. Someone put something in it, and now it weighs 40 pounds. What did the person add?

10. What is it that, given one, you’ll have either two or none?

11. What has 10 letters and starts with gas?

12. When you need me, you throw me away. When you don’t need me, you bring me back. What am I?

13. What kind of coat is always wet when you put it on?

14. I speak without a mouth and hear without ears. I have no body, but I come alive with the wind. What am I?

15. What can you hold in your right hand but never in your left?

16. When is a door not a door?

The Answers

1. A map

2. A fishhook

3. An artichoke

4. B (it’s surrounded by A/C)

5. A cloud

6. Water

7. Ice

8. Short (becomes shorter)

9. A hole

10. A choice

11. Automobile

12. An anchor

13. A coat of paint

14. An echo

15. Your left hand

16. When it’s ajar

Featured Image Credit: Martial Red/ Shutterstock

About the Author

Melanie Davis-McAfee

M. Davis-McAfee is a freelance writer, musician, and devoted cat mom of three living in southwest Kentucky.