How to write a riddle that’s meant to be solved
Riddles are a nearly universal form of puzzle, appearing in every language and culture throughout all of recorded history. Why are riddles so popular? For puzzle designers, they are often simple to construct, yet their difficulty can range from trivial to fiendish. For solvers, riddles offer the satisfaction of an epiphany. If you're planning a puzzle adventure, riddles are a fundamental tool, able to fit into almost any puzzle shaped hole. But for as flexible riddles can be, they can also be a dead stop to the fun if the players end up stumped. Whether you're writing a riddle or solving one, a good grasp of riddle construction will help you be your most clever.
The Anatomy of a Riddle
While riddles can appear in a wide variety of formats, almost every riddle can be broken down into a few common components:
The Premise - These are the details and information players are provided with. These details can be explicitly stated, or obscured through elaborate presentations or trickier logic.
The Structure - This is the pattern that the information fits into. Without a structure, a riddle is just a reading comprehension question.
The Ask - This is what the players are challenged to answer. Sometimes the ask can be implied by the structure, especially in traditional formats where players can be expected to recognize a shared structure.
Last Thing First
The best way to come up with a riddle is to start with the answer. This is especially true in a puzzle adventure, where the answer usually helps players find the next step in the adventure. Once you know what you want them to come away with, you can think about ways to obfuscate that information through logic, poetic description, and procedural manipulation.
A Premise Makes a Promise
The details in a premise are anything the player can trust to be true. Betraying this trust is the fastest way to write an unsatisfying riddle. But writing a good premise takes more than just a collection of details. Let's look at an example.
A flat approximation
of the rivers and the ground,
a projection with directions,
to help you get around.
What is it?
In this easy example, the first four lines comprise the premise. It's important to note that while there are only 4 lines to the premise, at least 5 details are divulged:
1. The answer is something flat
2. The answer approximates rivers and ground
3. The answer is a projection
4. The answer contains directions
5. The directions assist with navigation.
As a general rule, a riddle with more details in its premise is easier to solve than one with fewer. Each detail is like an answer in the game 20 Questions, it narrows down the scope of possible solutions. They are used by players to test the answers they come up with, knowing any answer which violates a detail in the premise should be rejected.
A good premise will have details that aren't just accurate, but evocative of the answer. Each detail should lead the player toward the correct solution, both logically and thematically. When this is done well, the solution will be "self-proving" to the player, meaning that when they come up with it, they *know* it's the right answer because it fits the whole theme. To give a counterexample, here's the same riddle above written with less evocative details
It can fit under a door
It rolls or maybe folds.
It helps you get to somewhere warm,
when you're somewhere cold.
While the answer is the same, this premise provides less thematic direction for the player to follow. We don't often think of the answer, which you can find below, as something that fits under a door, even though technically it could. And while you might use a one to "get somewhere warm", that's an unusual use case. This version isn't just harder, it's less fun.
Structure Sets the Stage
The structure of a riddle is the patterns it relies on to communicate the shape of the answer. It’s how you let your players know what to expect, and what to look for. In the above example, the structure is simple and traditional. There are four obscured descriptions of an object, and a challenge to identify it. Many riddles rely on a simple structure like this, with the more difficult versions offering fewer and more obscure details.
Nearly every reading person has encountered a riddle in this structure, so most people don’t need to be told “Each line describes properties of a specific thing. That thing may be a particular object, a category of objects, or even an esoteric idea or concept. Any thing that fits with all the of the descriptions is a good guess, but there’s one particular solution that fits best. The thing would be recognizable to any general person in your circumstances.”
Those implicit rules are part of the structure, hiding behind the words “What is it?” The structure lets the player know that “map” is a good guess, and “my friend Tom who shouts directions at me while I’m driving” isn’t. When Bilbo challenged Gollum with the riddle “What’s in my pocket?” Gollum’s rage comes from the violation of the implicit structure of the game they were playing. As a puzzle adventure designer, you want to avoid provoking rage from your players whenever possible.
Other riddle structures include “computational” or “procedural” riddles, where the player must follow a set of directions or keep track of a changing detail.
Every dwarf of 16 years is sent into the mine
with two friends, and two strangers following behind
The strangers are both older, but neither older than 19
the friends are both within a year of the leader in between.
Every dwarf responsible to bring back shiny gems
one for every year of age, plus 4 more for both friends.
With every member born in a different numbered year,
when they return from mining how many gemstones will appear?
In this example, the structure requires the player to plot the age range of the dwarves and add some numbers together to compute the solution. The structure assures players that if they come up with the right numbers and the right order of operations, they will arrive at the correct solution.
One wonderful thing about procedural riddles for puzzle adventures is that the numbers or details can refer to real world objects around your players. A detail like “The number of slides at this park multiplied by the number of trees” compels players to look around the park you’ve brought them to, which can be a great way to introduce the hook for the next puzzle.
Resist the temptation to use “gotcha” reasoning to solve a procedural puzzle. If you structure suggests that doing the calculations will get the answer, but it turns out the answer relies on tricky wording that doesn’t require any calculation, your players will feel almost cheated. In the context of a story or maybe a tabletop role-playing game, there’s room for this kind of trickery, but in a general puzzle adventure it’s probably a step too far.
Be Careful with Conundrums
Another structure you might encounter is a conundrum, which is the specific term for a riddle that relies on a play on words or a pun to function. Solving a conundrum is extraordinarily satisfying for a player up to the task, and you’ll see this type of riddle often as a way to test a hero’s wit in classic stories. Here’s an example:
What is shared by a tree and a dog?
The answer, which you can find below, is being used in two different ways at once. This property lets the player know they’ve found the answer. An answer like “shadow” may be technically accurate, but it doesn’t have that punning resonance that distinguishes it as the right answer. These riddles are especially popular in fiction, as they are compact and clever, and any hero solving one appears quite insightful. But they are notorious for interrupting a puzzle adventure when the players miss the key pun and instead get stuck on a wrong answer because they don’t know what’s missing.
If you include conundrum style puzzles, it’s wise to ensure that other thematic elements of the puzzle are pointing players in the right direction. You can go as far as to give a full example riddle with the answer already provided to teach your players the format, or you can make another puzzle mechanism that produces the answer through non-riddle means (like a cipher).
Just Ask
The ask is the way you tell your players what kind of answer you’re expecting. Your structure will help, especially if you’ve used an evocative premise, but it may be necessary to specify that you’re looking for a two word phrase, a famous character, or a type of food. Even a small change from “What is it?” to “Who am I?” at the end of a riddle can go a long way to getting your players pointed in the right direction.
In a challenging puzzle hunt for hardcore puzzlers, it’s common to skip the ask. The simple fact that there is a premise and a pattern is enough for some puzzlers to dive in and find an answer. But for a puzzle adventure, where the goal is to complete the challenge, it’s completely fine to be explicit with your ask. That can be as direct as “The answer is a valid English word of 8 letters”, or it can be more integrated like “Answer: _ _ _ _ _ _ _ _”. If nothing else, incorporating a few hint words in bold throughout the instructions text will give players some assurance that they understand what’s being asked of them.
Verification By Design
It’s important to consider your riddle solution, not just in terms of theme and challenge, but also in the way it communicates the next step to your players, and how they know when they have the right answer. Take this example:
In a park east of Main
with a tree that has a name
find the shortest towering pine
underneath a secret find
It may seem easy to write something like this (tailored to your play area), thinking “there’s only really one named tree on the east side of town, they’ll figure it out”. But think about what’s involved for a player to test their solution. And consider what happens when they guess wrong. If they don’t know of the named tree you had in mind, they could spend hours running around parks trying to find one. And every time they don’t find the right one, they are going to question if they’ve done something wrong, or worse, if you have.
In general, it’s probably not wise to have a riddle answer that is a location. It’s better if the riddle provides a code, password, or key that players can test easily where they are, and then for that prize to direct them to the location you want to send them too. Locations are better encoded into puzzle formats with clear, discrete solutions.
Another novice mistake is to rely on specific data from something that is onerous to search. “Riker’s Rank” is pretty easy to find on any Star Trek fan wiki. But “What Riker named his bug” might send your players through dozens of episode synopses or video essays looking for the one where Riker names his insectoid son Jean-Luc. Respect your players effort by avoiding difficult searches and allow them to easily test answers.
But Shouldn’t It Be Harder?
In a survey of people who would partake in a puzzle adventure asking how skilled they are at puzzling, the people who mark “Very Skilled” include both a group of people who participate in competitive puzzle events monthly, and a group of people that enjoyed a Sudoku book once in college. Remember that your ultimate goal when building a puzzle adventure is building a fun experience where your players overcome the challenges and win the day. You don’t win anything for stumping your players. It’s very easy to write a very hard riddle, and your players will only appreciate the high difficulty if they solve it on their own.
At the same time, a riddle on a piece of paper is not so exciting without a lot of thematic support. Writing out your riddles with a calligraphy pen on a parchment paper is definitely a nice touch, but it can only get you so far. To flesh out a riddle without just adding obscurity or difficulty, you can break the riddle up into pieces that the players must earn. A particularly useful version is a symbol cipher, like this:
In a ¤ or on a §
Turn it ¶, take a look.
What do you see?
For this example, you’d include other puzzles that taught what the symbols mean. As players discover that the symbols mean, in order, “body”, “book”, and “over”, the riddle’s solution comes into view. This is especially effective if the encoded riddle is provided early on with a promise that it will “make sense later”. That feeling when a player realizes they’ve just learned how to decipher a code they’ve held on to all day is very rewarding.
A well dressed riddle can even serve to let players know they are on the right track. When they put the pieces of a jigsaw puzzle together and discover a riddle written across it, they know they’ve found the next step of the adventure. A riddle that slowly constructs itself out of pieces as they progress can turn into a very exciting payoff when they finally have what they need to crack it.
The Difference Between Stuck and Stumped
When a player can’t progress in the Adventure because of a riddle, they are either stuck or stumped. A player is stuck when they don’t know the answer, but have an idea of things to try. They are stumped when they are out of ideas to try. A stuck player can be encouraged with a reminder, “Don’t forget about that cipher you learned earlier” or “Have you looked at all the maps carefully?” These hints feel encouraging because they let the player know they have what they need to make progress.
A stumped player needs a more direct hint “What kind of trees grow in the north?” or “Why is the second line phrased so oddly?” They need you to do a solving step for them to get them going again. And once they know that’s an option, you become a walking hint dispenser every time they get challenged, which is less fun for everyone.
How do you keep players from getting stumped? Try to minimize the amount of external knowledge your puzzles require. For example,
Aggassi’s necklace, when Dolly was born.
This (hard) riddle requires the player to know who Aggassi is, why they have a “necklace”, who Dolly is and when she was born. If you’re a fan of tennis and science headlines, this might not feel very challenging. But what if the only tennis players you knew were the Williams sisters? You’d need, at least, a web search to find out that Aggassi played tennis at the olympic level and that Dolly is a famous farm animal.
You might think “Ah, but my players have phones, they have internet, they can just look things up.” But then you’re creating a whole extra puzzle layer, perhaps unintentionally, where you are relying on your players to search for the right terms. It only takes one wrong search to send them off on a wild goose chase and derail your puzzle flow. And that’s all assuming that they even have reliable internet, that their phone is charged, and that the information you found online is still available when they go looking.
Of course, every riddle in this article relies on external knowledge to some degree. Determining what is “in scope” for your players can be very tricky. I like to use the “Dictionary vs Wikipedia” guideline. If the information could be found in a dictionary, and it’s not terribly obscure, it’s probably fair game for a general puzzle. If the information needed would be better found on Wikipedia, it’s probably not safe to rely on for a puzzle. In other words, players should be looking up words and meanings, not contexts and concepts. Not only does this help you keep your players on track, but you avoid the feeling that “the internet answered the riddle”.
If you’re writing a harder riddle, intending to send the players searching for external knowledge, it’s good to give them some guide as to where to look. For example, if your riddle involves world record trivia, it’s wise to specify whether you’re referring to the records kept by Guinness or the ones kept by the Book of Alternative Records. If your riddle involves identifying fonts by name, let your players know whether they should be looking at Google Fonts or the font list in MS Word. Knowing where to go looking shouldn’t be a part of the puzzle they have to solve for.
How to Hint
At a technical level, a puzzle is solvable when the players have what they need to discover the solution. But at a fun level, it takes a little more than that. People don’t like asking for hints, but they do like earning clues. You can use simple stunt challenges like “Carry this ice-cube on your forehead from here to the tree and back with no hands to earn a clue”, or you can use more elaborate constructions where the players discover hints in the play area around the riddle.
If players find your riddle next to, say, an Easter egg with the words “open me” written on it, that egg can contain a very basic clue. From there, additional clues can be hidden around in other eggs. Players can decide on their own how much energy they want to put into finding all the eggs and how much they want to focus on the riddle. Most likely, they won’t need to find all of the eggs, but even if they do you’ve built a path for them that requires no direct intervention. There’s a very exciting feeling when a player realizes they’ve earned “just enough” to crack a riddle without finding all the clues, it feels like finding a shortcut.
Bailing Out
Let’s consider the worst case situation: Your players have found all of your clues, they are reading everything clearly, and they are still stumped. They know they’ve been beaten by the puzzle, you know they’ve hit a wall, and the whole adventure is about to collapse in on itself. What should you do?
You could scramble, you could invent new ways to solve the puzzle on the spot and try to improvise your way to making them feel like they did something to earn progress. But this might feel like pandering, or even worse, like unpreparedness. No one wants to solve the “baby version” of the puzzle after being stumped, and trying to shoehorn in some plot reason to deliver the players the answer runs the risk of trivializing their work.
Instead, remember that the focus is the adventure, not the individual puzzles. In the interest of keeping the fun going, it’s OK to step in and bail them out. It doesn’t feel great, but it cuts the suffering off before it becomes a show stopper. When it comes to this, being simple, honest, and direct is the best approach. “I don’t want this to get in the way of the rest of the fun. Would you like to skip this puzzle for now?”
Don’t do a breakdown on the spot, just give them whatever information the riddle was meant to reveal. If they still want to revisit the riddle after the adventure is over, that’s the right time to walk them through it and discuss where it didn’t make sense. A post-event conversation is a great way to show that you care about your players and want to give them good experiences, even if one riddle fell short.
Putting it Together
So, to make a fun, solvable riddle, you need to consider:
How your players recognize your structure
How your players interpret your premise
How your players identify your ask
How your players seek additional information
And what you will do when they are stumped
You should be prepared to be tested on any assumptions you make. If you can point to a specific element in your adventure for each of those considerations, you’ve got more than a riddle, you have a plan for how to make a riddle work in your adventure.
Of course, if you’re putting a lot of work into a puzzle Adventure, playtesting is crucial. Getting external brains to work through your riddles is a really great way to find out when they are unexpectedly hard. It’s even better if you can get your riddle playtested by a few different people with different skill levels. You can always post on the Constructed Adventures playtesting thread on our Discord Channel.
Finally, once you’ve written and tested and polished your riddle, trust your work. Players rely on your confidence as a puzzle designer to feel safe investing their time in your adventures. If you undercut yourself by tinkering with the riddle or jumping in the first time they get stuck to walk them through it, your players may lose their trust that the adventure is ready for them to solve.
With careful planning, a good sense of what your players’ perspectives, and a bit of cleverness, you’ll can master the art of riddle writing. Use the styles and formats that appeal to you, write about the things that are interesting to you, and keep your focus on delivering that “Aha!” moment, and you’ll be delighting players time and time again.
The Answers
In case you got stumped, the answers are, in order: a map (twice), 93 gems, bark, spine, a gold medal.