• Hello game master! Welcome to our growing community. Please take a moment to Register (top right button, see how: Slides).

    If you use Campaign Logger, you can use the same login details - we've linked the app to this forum for secure and easy single sign-on for you.

    And please drop by the Introductions thread and say hi.

RPT Newsletter #005 | How to Turn Brain Teasers into Amazing Roleplaying Opportunities

Stephan Hornick

Community Goblin & Master of the Archive
Platinum WoA
Wizard of Story
Wizard of Combat
Borderland Explorer
How to Turn Brain Teasers into Amazing Roleplaying Opportunities
From JohnnFour | updated December 10, 2020

Roleplaying Tips Newsletter #005
Table of Contents
  • The Wise King
  • The Two Brothers
  • Death Meats the Squire

Puzzles are an essential part of roleplaying. Even in groups where puzzle solving is not preferred, the occasional rousing stumper creates some excellent variety. And variety is essential for keeping player interest in your game high.

While classic, dungeon-style puzzles are entertaining, my favorites are the ones that:
  • Encourage roleplaying
  • Allow you to roleplay out the solution
  • Integrate smoothly into your game (that is, they don’t jump out and scream “Puzzle!” at you)
  • Add to your story for greater campaign depth.
My best source for these kinds of highly enjoyable roleplaying brain teasers are puzzle & game books and magazines. Quite often you’ll find these books under the “Games” or “Hobbies” categories on the bookshelves. And don’t forget to check your local library.

I have no idea how you officially create your average brain teaser, but in my mind, I tend to divide them up into three parts: the Set-up, Method and Solution.

The Set-up tells you the parameters, or rules, of the puzzle as well as establishes who the participants are and the genre/setting. The key is to convert this information so that it is compatible with your game.

The Method is the way the people or objects in the brain teaser go about resolving the puzzle. This is the most important part because it is how your players, and their characters, will find and/or prove the solution. The best types of Methods are action oriented. Somebody has to do something. I find math and word puzzles generally make poor roleplaying puzzles because their Method is to just write figures on paper and perform mental calculations–not a great roleplaying opportunity

The Solution is obviously the answer to the puzzle. But it also contains the reward for success (you should make sure your puzzles always have a reward). And always be prepared and flexible to field alternate solutions–your players will be clever.

Here is an example from The Giant Book of Puzzles & Games, by Sheila Anne Barry, Sterling Publishing Company Inc., 1978 (I found this tome in a used book store last year).

The Wise King
During the Middle Ages, a Nordic king had a problem. His sons were good friends, and the king wanted to make sure that they would have no cause for jealousy after his death over the division of his property. He didn’t want to provide in his will merely that the possessions were to be divided equally, lest his sons start quarrelling over what each was to get.
Finally the king thought of a foolproof yet simple way of providing for absolutely equal distribution of his possessions. What did he write in his will?

The Set-up is to divide the king’s property into equal parts in such a way that there is guaranteed to be no future arguments thus helping the king feel comfortable about his will. The genre is already fantasy, but can be easily changed.

There are plenty of options for the Method. I could use any person or agency in my game world in place of the king, and would prefer to use someone of authority to increase the drama of the scenario: mayor, noble, master, mentor, patron, father, grandfather, employer, ally… I could even use a farmer sitting by the road weeping, troubled because he can’t figure out how to keep his family together after his passing which will occur soon because… etc. The players must hear the problem, discuss answers and present the solution.

To further thicken the plot, I could let the players know that they must present their solution in such a way so that they don’t offend the person with the problem. Perhaps because that person is touchy about people being smarter than him/her.

Or I could use an egg timer and provide a time limit–put some pressure on the players. Or I could have other parties compete for the answer: the king has asked the wisest men of his kingdom to hear his problem and present an answer.

The Solution has a number of potential rewards. The sons could be two of the players and they will only get their names in the will once the answer is found. Or perhaps there is a thank-you type of reward. What a great reward it would be to earn the respect and gratitude of your king. Or maybe the puzzle is just a test and will lead to further opportunities if passed.

Can you figure out a way to add a twist to your puzzles? What a great way to increase the drama, excitement and fun! For example, in the puzzle above, perhaps the king is interviewing 2 groups candidates for an upcoming, challenging mission–the player’s party and another party of heroes. But, the king wants the mission to fail, so he does *not* want to send the smartest party.

You leaked this information to the players beforehand–their task is to actually lose the puzzle to the other group because the mission, despite the possible sabotage, is still desirable.

So the king summons both groups, poses the problem and then waits for the answer. But, the other party honestly can’t seem to find the answer. They’re stuck. What will the players do? A fun twist!

Here are two more puzzles, from the same book, for you to roleplay with:

The Two Brothers
A Saxon king, displeased with the greed shown by his two sons, left a will with an unusual provision: The sons were to mount their horses in a tiny town on the border of the kingdom and ride, without dismounting more than once, to the gate of the king’s castle. The son whose horse arrived *second* at the castle gate was to be awarded the entire fortune.
When the king passed away, the sons began their “race,” moving along slowly together for days on end. Each tried to go slower than the other and after a while, they got so sleepy they had to dismount and get some sleep at an inn. While they slept, they each had their footmen alerted to notify them when the other left the inn. Actually, they left the inn together. As they were about to mount their horses, one brother whispered a few words to the other, they both laughed, jumped into the saddles and raced the horses as fast as they could to the castle gate.
It doesn’t matter to us which brother won the fortune, but can you figure out what the brother whispered?

Death Meets The Squire
In a small English town long ago, this story was told: It was a hot summer Sunday. The squire and his wife were in church when the squire fell asleep. He dreamed he was a French nobleman at the time of the Revolution. He had been condemned to death, and he was waiting on the scaffold for the guillotine to fall. Just then his wife, noticing that he was asleep, tapped him sharply on the back of his neck with her fan. The shock was so great–in view of what he was dreaming–that the squire immediately slumped over, dead.
Could this story be true? Why?

Try one of these puzzles at your next game session and let me know how you changed it and what your experience was.
Last edited:

Stephan Hornick

Community Goblin & Master of the Archive
Platinum WoA
Wizard of Story
Wizard of Combat
Borderland Explorer
Riddles are a great element of roleplaying games IF used correctly. Else, they can destroy the pacing and the mood.
So, here are the main elements, you HAVE to be careful about, according to Paul Camp, a game designer who is specialized on puzzles and riddles in roleplaying games: Dungeonvault:
  • Avoid letting the players get stuck.
    Make a series of easy to solve puzzles which build on each other to show progress.

  • Create a cooperative experience.
    Have the players (and PCs) cooperate, do not let one player solve it.

  • Challenge the players and the characters.
    Let this be a challenge for players and characters alike, so that it is not only the players who are playing a separate game, but include the PCs and their skills for success.

  • Create an immersive puzzle.
    Fit the puzzle into the setting in a natural way, make it a social puzzle, a skill puzzle, an actual door puzzle, or whatever, but don't just hand out a sudoku, which is completely unrelated to the roleplaying experience and will break the immersion.

  • Layer puzzles.
    If you layer different puzzles you can create diversion and also gradually increase the difficulty.

More details and examples you will find on Paul's site.

And here once more, Paul's summary of the most important things to keep in mind:
  • Easy to solve
  • Create many steps
  • Start designing at the end
  • Create a visual puzzle
  • Create key pieces and clues
  • Make players work together
  • Incorporate skill and ability checks
  • Bypass the puzzle at cost
  • Have a logical reason for why the door is locked by a puzzle
  • Create urgency
  • Make opening the door matter to the PCs
  • Layer door puzzles
  • Let the D&D story flow with the path of doors