How to make good riddles in D&D

Making good riddles in D&D is hard for some dungeon masters. Myself included for the longest time. This is, until I learned a few tricks.

Making good riddles in D&D should involve options for the player. Either the riddle needs to be open-ended or there should be alternative solutions.

We are shown many classic examples with riddles having only 1 answer. It seems like a good idea, but it is terrible for your game.

Why 1 answer riddles are bad

“I can crawl, I can fly, I have hands but no legs or wings either. What am I?”

The answer to this riddle is time, but players could come up with a different answer. Players can also point out that time does not have hands but a clock does. Therefore, the answer is a clock. But wait! A clock can’t fly or crawl that is time, so what is it?

Your players can end up discussing for hours what the answer is and not get it right. Sometimes the players psych themselves out of the answer and give the wrong one. This is why having a traditional riddle with 1 answer is not the best, but there are worse outcomes.

Your players do not know the answer. They never guess it and the game grinds to a halt. What do you do now? The players have to guess the riddle in order to proceed and you cannot just give them the answer. The players will feel like this was all a stupid waste of time if you give them the answer.

Riddles in D&D are based on puzzles. Riddles are a different form of puzzles which is why most people get this confused, but Wikipedia agrees with me so that statement cannot possibly be false!

Don’t worry, it isn’t just Wikipedia. There are other sources like Merriam webster that agree.

Riddles are just different forms of puzzles. You should follow the steps on how to create a good puzzle before you start crafting a riddle. Start by reading this article on puzzles.

If you took the time to read that article you will see some correlation between what makes a good riddle and what makes a good puzzle.

These are 2 completely different terms though, so we should get into the difference between puzzles and riddles.

Puzzles vs riddles

Puzzles are objects that are used to test a person’s mental capacity.

Riddles are questions that are used to test a person’s mental capacity.

Both are used to test a person’s mental capacity but are very different. It is akin to how a sword and a spell deal damage, but how the damage gets there is different and important.

Puzzles let the environment trick a person and pit the players against an unyielding object. Riddles are usually administered by a person or are written.

Some people would say that you can do more with puzzles than riddles. To a certain extent, they are right. You cannot have a variety of challenges with riddles that you can with puzzles. With a puzzle, you can set a room to kill the players or just reset until the players figure it out. Puzzles can have more varied end results but riddles can evoke more thought.

Players with puzzles try to solve the puzzle and usually do so with a sense of duress. They are timed or feel timed to solve puzzles and have to work quickly.

Riddles, on the other hand, are generally meant to be pondered over. The people or object asking the riddle give the players enough time to adequately think of the answer.

This is because riddles generally only have 1 answer in traditional settings. Riddles also are a mental challenge that forces you to really think about every aspect of the riddle. A puzzle can be flip the switches or try try try again to figure it out.

Puzzles can require a party to take more time to figure it out, but usually, anything that has a calm atmosphere to figure out the problem is referred to as a riddle.

There is one problem with making good riddles D&D.

Riddles are hard

When we talked about the 1 answer riddles there was an example. This example did not give you the answer and the answer was debatable.

For that reason alone you should not give 1 answer only riddles. I suggest leaving it open-ended for your players to think about it and give their best answer. If they are anywhere near the mark, give it to them. If they are way off, have them try again.

Why do I suggest doing it this way? Think about it from the player’s perspective.

They are overthinking this riddle, discussing amongst themselves, and they have to guess exactly what you are thinking. If none of your players are psychic, this can lead to problems.

The answer is time but they give their answer as a clock. That isn’t good enough so they come together and think that it is age. This is not good enough. Another attempt makes them think of father time. This is not good enough since it isn’t time. Everyone is now frustrated and they don’t want to guess again or continue with the game.

This is what happens when a riddle is done poorly and no one is psychic in your group. Good riddles in D&D are hard. If you want a great example of some other riddles check out the riddles section in the RPG companion app or any of the other riddles online. Go check them out and come back when you have read a few.

When you read the riddles either you knew the answer or had absolutely no idea what the answer was. Once you learn the answer you are either validated with it being ‘too easy,’ mad at how stupid the answer is, or go ‘awweeeee’ in agreement but would in reality never guess it.

Each person is different so what is difficult for one person might be easy for another. Riddle guessing is also not an art that many people actively pursue in our society. Since people are not experienced in guessing riddles they are most of the time a terrible at guessing the right answers.

Because of all these reasons answering a riddle correctly is hard. Riddles are hard and it is, therefore, hard to make good riddles in D&D. If you want a good example of riddles, our affiliate at Dungeon Vault has some riddle cards that can be useful to you and give you an idea of how to make riddles.

When making good riddles in D&D I highly suggest that you instead follow this method.

Alternative progress and options

Riddles and puzzles should never be used to gate progress. If players have to answer a riddle in order to progress then something is wrong. Soon that something will be your game as players get frustrated and want to quit or you are mad at a riddle being too easy. Aside from this though, required riddles are a bad idea.

I just went over the last section of how riddles are hard. There are many potential problems with riddles. D&D is also not a game about following the bread crumbs to make the pre-written story come to life. You are working with players who also shape the story. Therefore, you should always have alternative ways to further the story.

If you ever put forth a riddle for the party make it optional. The party might need to solve a riddle to open a treasure room door. If they can’t solve it, great they don’t get some treasure. They are still able to progress and just lose that part of the story.

If you want the players to solve a riddle in order to progress put a riddle early in the adventure on the wall. Have the riddle repeat later when the players need to solve it. By this time the players should have been given a lot of time to stew on it and think about the answer.

If your players still cannot think of the answer let them find a secret door that has a more hazardous path. Let the players know that solving the riddle was the challenge for that part. If they solved it they would have overcome that challenge. For a new path, there is a different challenge. That is the only difference.

If you are concerned about making good riddles in D&D always make an alternative. Even if you know that your riddles are amazing make an alternative option or 2 for the players. I recommend 2 alternative options since players may not know the riddle, can’t think of finding the alternative and eventually they will find the 3rd.

Riddles don’t just have to be gates though!

Riddles enriching your game

When people think of using riddles they think of making riddles to gate something. Forward progression is gated by solving a riddle. A secret room or item is gated by a riddle. They are basically a fancy lock.

Riddles can be more than this.

Making good D&D riddles can enhance your world if done correctly. A mysterious riddle can lead to a creation myth that takes your party to an ancient continent. The players can learn about the gods from a riddle. Players can learn about a culture from a riddle. There are many ways to use riddles other than fancy locks!

Think of prophecy. Prophecy is a sort of riddle 90%+ of the time. Prophecy is different than most riddles since it might come true, but your riddles might also contain information. If your players find a riddle that is obscure and want to solve it, let them and have it lead to another adventure or an important lore revelation.

Conclusion

I know this is a bit short but making good riddles is simple.

1. Leave the answer to be open-ended.
2. Don’t just use riddles as gates. They can enhance your world.
3. Allow alternative. Do not let riddles be the only way to progress.

Always keep in mind that riddles are hard!

Players will do their best but sometimes it isn’t good enough. When a riddle doesn’t click with them or they cannot read your mind things can go bad. Just keep these 3 rules in mind when making riddles. If you remember these 3 rules you should have no problems when making good D&D riddles.

This has been Wizo and keep rolling!