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The Complete Guide to DnD Riddles

by MTDadmin
dnd riddles

While not always employed effectively, riddles have a long history in role playing games. But how do you create DnD riddles?

Fantasy classics have great examples to pull from, most notably The Hobbit with the riddles Bilbo gives to Gollum.

A box without hinges, key, or lid,

Yet golden treasure inside is hid.

Spoilers: the answer is an egg. This classic riddle is a great example of the kind of riddles that can make great additions to your DnD games. When used properly, these simple linguistic puzzles can add a fun diversion from the senseless mayhem your players unleash on the world. When used improperly, a riddle can cause your game to come to a screeching halt. Let’s dive into how to use, create, and effectively weave riddles into your DnD game.

What Makes a Riddle

A riddle is a statement that describes something in a way that requires thought, understanding, or context clues to guess what it describes. While there are a lot of different types of riddles that exist in varying complexities, the core idea is to guess what the riddle is referring to.

While not necessarily required, most riddles use obtuse or metaphorical terminology. In the example earlier from The Hobbit, an egg is described as a box. This is literally incorrect in a geometric sense, but when using the word box to mean a container, it is roughly true. This brings us to our first key components to riddles: abstraction and metaphor.


Abstraction is the process of removing characteristics from something in order to reduce it to its essential characteristics. Our example from The Hobbit abstracts that an egg is a container and then substitutes the word box. The substitution highlights that abstraction alone does not make for a good riddle.

If we were to simply abstract from the answer “an egg” we would get down to a container. This is too vague, and abstracting yolk down to a golden substance is still not really that much of a riddle. Without metaphor or substitution, a riddle never really has a leg to stand on.


A metaphor is a way to describe something through a non-literal comparison, typically highlighting a way in which two things have similar functions or qualities.

To build a proper riddle you need to use metaphors to construct an additional layer into the riddle and make it approachable. While metaphor can make a riddle more difficult to approach, it also acts as a way to present clues by giving you a grounds on which to compare to the answer.

Back to our example from the Hobbit when the egg is metaphorically a box. By establishing this comparison we then have room to use metaphor to not only compare, but also contrast the two items. This provides a structure to think about the answer. While an egg is like a box in that it is a container, it is unlike a box in that it has no means to open and close it.

Additional Clues Through Description

While riddles can simply be a metaphor of an abstracted object, they really only become good riddles when you give more hints through the additional layers of description. In our Hobbit example that comes in the form of ‘’yet golden treasure inside is hid.” The riddle arguably would have been solvable without that additional item. However, the presentation of more information elevates the riddle from esoteric to fun by narrowing the possibilities.

Now we need to discuss absolutes. While a riddle is cryptic, our additional information must always be true. A fair riddle never provides a “sometimes” characteristic. All eggs have yolks, so the golden treasure hint provides information to narrow the results. Make sure your hints always narrow your possible answers and don’t open to even more possibilities.

Simple Answers

The final characteristic of riddles is that they tend to have simple answers. A riddle cannot be too specific because then it becomes inaccessible to people without knowledge of a topic. While you can make riddles with complex or specific answers, you will need to provide that information beforehand or give additional context clues in the presentation of the riddle.

The very best riddles have common objects or concepts as answers. An egg, time, the sun, etc. These ensure that anyone interacting with the riddle will at least have a chance of answering it correctly. It also allows for a fair understanding of the scope of the answer. People generally expect the answer to a riddle to be a one word solution.

How to Make a Riddle:

Now that you know what a riddle is and how it’s made up, let’s look at how you create one:

  1. Choose your answer
  2. Reduce the answer to its simplest concepts (Abstraction)
  3. Use a metaphor to describe the answer
  4. Add a statement that contrasts the metaphor
  5. Provide an additional hint using metaphor, simile, or other word play

Let’s go through the process together with a new example:

  • Answer: A lighter
  • Abstraction: a tool that makes fire
  • Metaphor: A metallic dragon
  • Contrast: Small in size
  • Additional Hint: a tool => tamed by man

The final riddle becomes: A metallic dragon, small in size, tamed by man. The answer is a lighter.

While we made this a DnD themed riddle, it can really be anything so long as the riddle’s concepts are understandable to the audience.

How to Use Riddles in DnD

Understanding what riddles are and how to craft them is only the first part of your journey when blending riddles into your DnD game. Dungeons and Dragons is a perfect setting for riddles, but when used improperly they can bring your whole game to a grinding halt. Let’s look at a few simple rules to follow that will keep you out of trouble.

Don’t Place Riddles on the Critical Path

When using a riddle in your game, never make them necessary for your game to move forward. This is the same advice we give for puzzles. While you might have the utmost confidence in your player’s ability to solve a riddle, they might not be able to. Riddles are great for optional rooms, side paths, and alternative solutions to a quest. But if you block your main path off with one and your players get stuck, you’ll have to figure something out to keep the story moving.

Limit Answers

Put some pressure on your players! You don’t need to give them a timer for riddles, but also don’t give them the opportunity to answer endlessly. Riddles take time to think about, but sometimes players will just try any answer if they can and shout out a list of one word answers or concepts.

If a riddle exists there should be a cost associated with wrong answers. This makes your players think and also limits their guess to the resources they have available, be it gold or HP. Players will either walk away if they get stuck or will think more carefully and come back later. Springing a hidden trap could be an excellent consequence for too many wrong answers.

Additionally, if a player comes up with an answer to your riddle that wasn’t the answer you had in mind but is still an excellent fit, give it to them. This helps speed up the game tremendously.

Ask Your Players to Discuss in Character

Nothing causes meta gaming quite like a riddle or puzzle room. If your players are going to think about it and share ideas and information, ask them to do so in character. This will keep them in the game and stops them from coming up with answers based on the real world rather than the fantasy one.

Once players start meta gaming they quickly start trying solutions that are out of place or require knowledge their characters would never have. Asking them to discuss in character helps ground them and keeps the game alive.

Reward Correct Answers Appropriately

Nothing is a bigger bummer than getting no reward for doing something that was hard. Riddles take thought, ingenuity, and a certain amount of focus from the players. This effort should be rewarded.

It doesn’t have to be treasure; it could be lore, new pathways, or optional quests. Just make sure there is something to be gained from putting in the effort. Players hate that “the real treasure was the friends you found along the way” schtick if it’s not used with great care.

Go Make Some DnD Riddles

Now that you know the process, try to craft a few riddles of your own. They can seem intimidating at first, but with the simple guidelines created here you can easily craft a few to use in your game. If you follow our advice you’ll be on your way to crafting and implementing amazing riddles in your game. We’d love for you to tweet your creations at us @masterdadungeon and see what you come up with!

For more walkthroughs and trap examples, check out our Complete Guide to DnD Traps article.

Happy DMing!

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