The Ancient Game of Riddles
A riddle-making game for matching wits with fictional fairytale foes.
“‘Both wrong,’ cried Bilbo very much relieved; and he jumped at once to his feet, put his back to the nearest wall, and held out his little sword. He knew, of course, that the riddle-game was sacred and of immense antiquity, and even wicked creatures were afraid to cheat when they played at it. But he felt he could not trust this slimy thing to keep any promise at a pinch. Any excuse would do for him to slide out of it. And after all that last question had not been a genuine riddle according to the ancient laws.”
— The Hobbit, J.R.R. Tolkien
The riddle is a test of worthiness. The riddle is the guardian standing at the doorway to mystery. The riddle is a contest of great stakes between adversaries in wisdom and willpower. The riddle is a pastime of friendly boasting and bonding between old and new friends by a fireside.
Tabletop roleplaying games, particularly those downstream of faerie tale and “Tolkeinesque” fantasy, often include riddles as tests for player characters. Typically, the game will pose a literal riddle for players to bash their heads against or, in the case of Free Leagues The One Ring, gives you a skill called “Riddles” and you can simply make a Riddles Check to see if you are victorious.
To my yearning heart, neither of these approaches gives the feeling of creative puzzling, journeying wit, or sudden triumph that I desire from a folkloric tussling of minds.
I am proposing a small procedural game to replace these methods wherever you find them. In stark contrast to those game mechanics, the Ancient Game of Riddles invites players into the fun of puzzling not by asking them to solve a riddle, but by asking them to design one.
Let’s play…
Playing the Ancient Game of Riddles
The game begins when, through the course of normal repartee, one fellow proposes a game of riddles to settle a dispute or content. The adversaries in the game should negotiate the terms of victory or some prize to be won. One player, representing his side, begins by Composing a Riddle, then Gathers the Stones, and then Matches Wits to see if the game continues or concludes.
Compose a Riddle
The player matching wits against the adversary in the ancient game first spends ample time inventing a riddle, leading a collaboration with the other players.
The player begins with an answer. Answers can include:
Everyday objects: a key, a candle, a thorn, a comb, a door.
Elements of nature: an echo, beasts, a pine tree, a hidden stream, a star.
Abstract concepts: time, age, silence, a secret, memories, today.
Places: a guest-house, a cemetery, a library, a bridge, a well.
People: a tax-collector, a butcher, a bee-keeper, death.
Containers and keeping-places: a book, a deck of cards, a footlocker, a map.
Particularly clever riddlers might use local legends or place names from your game world as the answer, such as “The Good King Medwyn” or “The Owereth Forest.”
Then the player designs a riddle. Riddles have many schemes:
Enigma
A poetic description that twists around the expected, so you always lose its trail. To design this riddle, brainstorm many features of your riddle’s answer. Then, list them, and find twists on these features to obscure their nature.
What runs, but never walks. Murmurs, but never talks. Has a bed, but never sleeps. And has a mouth, but never eats? (a river)
I have keys but no locks. I have space but no rooms. You can enter, but you can’t go inside. (a keyboard)
Narrative
The narrative riddle might be a process, a life cycle, a passage through time, or simply how an object changes as we encounter it. With your riddle answer, sketch out a way your answer changes over time, and then find a simple story that tells that change symbolically.
Thirty white horses on a red hill. First they champ, then they stamp, then they stand still. (teeth)
I am born in the sea, live in the sky, and die on the earth. (rain)
I am taken from a mine and shut up in a wooden case; I never see the sun, yet I help others to see. (the lead in a pencil)
Paradox
The paradox describes the answer in simple terms, but in a way that uses wordplay to create a contradiction. These are difficult to design!
The more you share me, the less I am. What am I? (a secret)
The more you take, the more you leave behind. (footsteps)
Once you have your riddle, write it down or compose it well so that it can be said aloud clearly. When the player is finished, they can recite the riddle to their adversary. Then, gather the stones.
Gather the Stones
For your stones, gather at the table two sets of tokens of equal size and weight, but in two distinct colors — poker chips, playing cards, mancala beads, or dice of a uniform size will all work. You will be gathering them into a pool together.
Begin with 1 red and 1 white stone in the pool for each player.
Add 1 white stone if the riddle rhymes, or is in a pleasing meter.
Add 1 white stone if the answer to the riddle is a specific object, person, or place known to legend, history, or local custom.
Add 1 white stone if the riddling character is a particularly proficient riddler compared with the adversary.
Each player may add 1 red stone if they believe the riddle is either too obvious or too obscure to be reasonably guessed by an average wit.
Each player may add 1 white stone if they believe the riddle is tricky, but guessable given some time to ponder.
Once you’ve completed the pool of stones, put them in a gathering place like a hat or a bag. It’s time to match wits with the adversary.
Match Wits
Mix the stones together in secret, so that the adversary can draw stones without looking. Two stones are drawn, one after the other. Interpret the results below:
WHITE…
The adversary cannot guess the riddle…
….then WHITE
The adversary concedes that they are no match for the riddling character’s sharp wit and clever tongue. The riddling character triumphs!
…then RED
The adversary demands another riddle so they might have a fair shot. The game begins again, but for the rest of the game, begin with only 1 red stone in the pile, instead of 1 red stone for each player.
RED…
The adversary correctly guesses the answer to the riddle.
…then WHITE
The adversary insists on another try, or else takes their own turn, depending on their nature. The game begins again, perhaps with the roles of riddler and adversary reversed.
…then RED
The adversary declares themselves the victor and insists on their prize.
The Ancient Game of Riddles, in part, uses the Red & White rules from Follow: A New Fellowship by Ben Robbins, lamemage.com.
More notes
Maybe I should flesh this riddle out, put it into a little tiny zine, and hand it out at PAXU or something. I don’t even have tickets yet.
I’ll be at ArcaneCon in Northampton, MA, November 7 & 8! I’m running Mythic Bastionland for whatever three players show up and register. I’ll have to prep and do a quick playtest of the one-shot I’m going to run. This post got me thinking that maybe one-shots should really be structured in a way more divergent with a first session of a campaign than I am initially inclined.
I’m glad I wrote this little game, maybe now I’ll finally be ok with running The One Ring. Except I’m too desperate to run shorter CfB games instead, like By Endurance We Conquer. Anyhow, I’ve actually had this game on my mind for a year, but I went on a beautiful hike today and fleshed it out while walking, so here it is.
Speaking of which, go back The Girls of the Genziana Hotel by Hendrick ten Napel. It looks so fucking good! And it’s already done, “backing” it just means buying the zine.
The illustration at the top is Bilbo and Gollum by Cor Blok. I love historical takes on illustrating Tolkien.