Riddles in Roleplaying

A riddle is a statement or question or phrase having a double or veiled meaning, put forth as a puzzle to be solved. Riddles are of two types: enigmas, which are problems generally expressed in metaphorical or allegorical language that require ingenuity and careful thinking for their solution, and conundrums, which are questions relying for their effects on punning in either the question or the answer.

The former type, enigmas, are often the most-used type in fantasy roleplaying, thanks to their heavy usage in J. R. R. Tolkien’s The Hobbit, which in turn was inspired heavily by Norse mythology. In fact, the scene in The Hobbit where Bilbo wins the One Ring from Gollum was a mirror of Odin winning such a contest by the (rather questionable) tactic of asking a question to which only he could know the answer.

In roleplaying, riddles can be a dynamic tool as well as fun. While they work best in fantasy settings, they can be used in modern ones as well. While some players do prefer their characters to be able to solve the puzzle based upon their respective stats, a lot of them enjoy the fun of a good brain teaser. And if the riddle is too hard, there certainly shouldn’t be anything wrong with them asking their fellow adventurers for help.

Here are some examples of riddles, along with the answers (which can be seen by highlighting the text following “Answer:”:

1. Often talked of, never seen, Ever coming, never been, Daily looked for, never here, Still approaching, coming near. Thousands for it’s visit wait But alas for their fate, Tho’ they expect me to appear, They will never find me here.

Answer: Tomorrow

2. I never was, am always to be, magicians say they can see me, but none else ever will. And yet I am the confidence of all to live, I am the hope of the poor and the doom for the rich. What am I?

Answer: The Future

3. I’m the one that death can’t find, I make you laugh, I make you cry. You will met me more often in your older days because then i have more to tell.

Answer: Memories

4. My host thinks I’m an irritation, a bother, a pain. But he can’t evict me, so here I will remain. Then one day I’m taken and ranked among my peers. Can you guess just what I am? Then you might call me dear.

Answer: A Pearl

5.My thunder comes before my lightning. My lightning comes before my rain. My rain dries up all the land it touches. What am I?

Answer: A Volcano

6. No legs for me to dance.No lungs for me to breath. No life for me to live or die but yet i can do all three.

Answer: Fire

7. I’m old and it feels like i have run forever, but never moved at all. I got no lungs or throat, but still I have mighty roaring call. What am I?

Answer: A Clock

8. I have four wings, but cannot fly, I never laugh and never cry; On the same spot I’m always found, toiling away with little sound. What am I?

Answer: A Windmill

9. Almost everyone sees me without noticing me, for what is beyond is what he or she seeks. What am I?

Answer: A Window

10. I make you weak at the worst of times, but I keep you safe, I keep you fine. I make your hands sweat, and your heart grow cold, I visit the weak, but seldom the bold. What am I?

Answer: Fear

11. I dig out tiny caves, and store gold and silver in them. I also build bridges of silver and make crowns of gold. They are the smallest you could imagine. Sooner or later everybody needs my help, yet many people are afraid to let me help them. Who am I?

Answer: A Dentist

12. I have no voice and yet I speak to you, I tell of all things in the world that people do. I have leaves, but I am not a tree, I have a spine and hinges, but I am not a man or a door, I have told you all, I cannot tell you more. What am I?

Answer: A Book

13. I have a few feathers to help me fly. I have a body and head, but I’m not alive. It is your strength which determines how far I go. When I’m along your side, You decide who lives or die. What am I?

Answer: An Arrow

14. A warrior amongst the flowers, he bears a thrusting sword. He uses his life to defend his golden hoard

Answer: A Bee

15. I’m just a hole tied to more holes; I’m strong but not stronger than my weakest friend, and of course not as stiff as a pole. What am I?

Answer: A Chain

16. Many men has died because of me, thou I’m a lot smaller then them. I’m often carried around with my brothers, just to show who is the mightiest. I have the greatest power when given away, yet lust for me keeps me locked away. What am I?

Answer: A Coin

17. What has six faces, but does not wear makeup. It also has twenty-one eyes.

Answer: A Die

18. My voice rises above the din, Sometimes catching all unaware. I never ask questions, yet get many answers. What am I?

Answer: A Doorbell

19. What is more useful when it is broken?

Answer: An Egg

20. I am as cold as death, and not breathing air. Never thirsty, but ever drinking. Covered in mail, but never clinking. What am I?

Answer: Fish

21. A strange thing, the more you take, the more you leave behind? What can this be?

Answer: Stairs

22. My life is often a volume of grief, your help is needed to turn a new leaf. Stiff is my spine and my body is pale, but I’m always ready to tell a tale. What am I?

Answer: A Book

23. Light as a feather, but yet a strong man can’t hold it more than a minute or two. What is it?

Answer: Breath

24. What traps warmth, sprays forth ice and water, yet slips through your fingers with ease?

Answer: Clouds

25. A little pool with two layers of wall around it. One white and soft and the other dark and hard, amidst a light brown grassy lawn with an outline of a green grass. What am I?

Answer: A Coconut

26. I’m old and it feels like i have run’ forever, but never moved at all. I’ve got no lungs or throat, but still I have mighty roaring call. What am I?

Answer: A Waterfall

27. What is greater than the Gods of Valhalla and more evil than the Devil himself? The poor people have it in loads, but the rich have to ask for it. And if you eat it, you’ll die?

Answer: Nothing

28. I move without wings, between silken strings, I leave as you find, my substance behind. What am I?

Answer: A Spider

29. What is too much for one, enough for two, and nothing at all for three?

Answer: A Secret

30. I come out of the earth and am sold in the market. He who buys me cuts my tail, takes off my suit of silk, and weeps beside me when I am dead. What am I?

Answer: An Onion

For other extensive sources of riddles, the Thieves Guild and The Berkeley Riddle database are excellent sources of riddles that can be incorporated into any RPG by DMs of any level.