Riddle Contests, An Attempt
“Guessing what’s in the GM’s pocket” is derived from a famous “neck riddle” in The Hobbit. Neck riddles are by design impossible to solve, built on hyper specific events known to only the speaker. Translated from literature to tabletop gaming this phrase represents bad game design where players are asked to guess the content of the GM’s mind to get an exact solution to a problem. If you do not like solving them, any riddle-locked door or enigma-rich sphinx the GM puts in front of you feels, rightly, like mind reader bullshit.
Downstream of Goblin Punch, riddles are obstacles testing something like “wit” that should be supplemented with parallel tracks to navigate them by. This is not a framework conducive to players choosing to actively search the game world for riddles to be used in contests they plan to instigate. How, though, do I weave this practice in without falling into a pocket tailor-made for my own hubris? I need a framework first to make riddles into something players dig through the world to find, and treat as tools to achieve their own ends.
Riddling practices of all kinds have a discursive function for those who participate. While there are literary riddles, riddling often emerges first from oral traditions. They record proverbs and history, affirm or contest moral and cultural norms. At bare minimum riddling demonstrates in-group kinship, a metaphorically laden common sense. By learning their riddles, you can get closer to the people you learned them from. Viewed this way, riddle games offer us a new kind of test: in-world cultural competence, socially rewarding the curiosity to find and use riddles in the right context.
With the framework and test established, this is how I’m planning to implement it. During world building pick out some immediately relevant cultural blocs, factions, and/or languages spoken if language skills matter for your table. Write out the basic relationships these cultures have, then figure out 1 to 3 thematic categories each of these groups individually riddle about. Lots of riddles are about everyday concepts relevant to people’s lives: Mountains, Forks, Chairs, Swords, Time, Sex, Death, Cows, Kings, etc. Say for a village of peasant farmers their riddles could be about farm and home, natural features, and sex riddles– everyone loves a dick joke.
Then, construct the first 1-3 riddles for each theme. While there is no universal, structuralist, answer to what a riddle is that applies to all cultures, we can prune some nuance to make our riddling hedgerows into fine topiary.
Here, a bit of Tolkien.
“Box without hinges, key, or lid, yet gold en treasure inside is hid – what am I? (An Egg).”
There are three devices in this riddle:
An Image. A box and golden treasure.
A block or contradiction in the image, that pushes us to think metaphorically. “A box without… yet golden…”
The Answer. “An egg”.
An example I wrote using this structure: “Five travellers this saddle carries without need of horse to ride. When you stand tall, I lay flat, what am I? (A shoe).”
Much like spies engaging in call and response to confirm their identities and transact business, casual riddling provides permission to work together. Sharing a riddle entails communicating some cultural norms such that the other sees you at least as “getting it” depending on the riddle you tell, even if they don’t know the answer.
At the start of a game, if PCs have a background tying them to a culture, or who are fluent in a given language skill, ask if they want to know a riddle from those blocs or make one up! This is a great chance for some collaborative world building (or not). If they choose either, have them write it down, as well as the culture of origin, on a party-wide Riddle Book document. You should have them do this whenever a new riddle is introduced, for their convenience.
When you first share riddles with an NPC outside of a contest it affects their disposition.
If it’s of their culture or a friendly one they move one step friendlier! If it is from a culture they don’t trust, make them more suspicious or hostile. Provide nuance and emotional complexity to this binary as you need, or via any disposition system of choice. If the NPC fields the riddle, and the PCs don’t offer one in kind, you get the disposition boost if you guess their riddle correctly. All the same, ride it out in the fiction.
This should provide a meaningful incentive to learn local riddles while traveling, and get players to reach for these as a broad tool. A riddle always provides a one-time window of opportunity to talk to NPCs on more positive terms or improve later odds for social-outcome dice rolls. All you need to do is hear the image, along with the answer, in the environment, and you have it forever! You can squeeze them out of demons in your abyssal dungeon to later buy time against an unfair boss! Re-encountering the sleepy Troll, before a surly grump. With a goblin riddle there’s space to talk, wherein it tries to parley you into feeding it the wizard’s familiar.
By learning riddles you are also equipping yourself to enter into a riddling contest. The riddling game can be used to settle disputes too petty for village elders, and if given their ear, can bend the will of kings and dragons. To extract demands on the basis of this honor bound guessing game is where you cash out the time and attention invested in gathering riddles, and stake your newfound reputation.
When a player or NPC challenges someone to a riddling game, establish what each side gets if they win. By default either can always decline the contest without penalty, so make them want to do it. Flip a coin for who fields the first riddle. The side that fails to guess an answer or proffer a new riddle first loses the contest. Riddling contests are 1v1 affairs, but clearly there is a group intelligence across from the GM and the players should coordinate to solve the riddles even if one character is the mouth piece.
The PCs should have a number of free guesses based on the stats of the character participating and the number of riddles gathered. Think of it as deliberating on a hypothesis before speaking. Using a DnD equivalent? Look to their Intelligence modifier or your game’s equivalent stat– they get that many free guesses per riddle. Aim for a range between 0-5 freebies from stats, so you might have to do some math depending. For Mythic Bastionland I’d Offer 1d4 Clarity loss in exchange for free guesses. Maybe offer a Clarity test to not suffer the stat loss until they fail, so they can make even more free guesses. Think of other resources you can tax in your game of choice and exchange them for free guesses if that fits the tone. In HMTW it might take time, so torches gutter as you puzzle over how exactly a raven is like a writing desk.
Additionally, for every three known riddles that share the culture of the riddle being guessed, you get one more free guess
The length of the contest should be set depending on the age, intellect, and worldliness of the NPC riddled against. Give them anywhere between 1-5 exchanges they can handle at most. An ancient lich or grand dragon is well stocked on riddles, but a humble goblin might only have one turn on the carousel before they fall off. At the high end, if the PCs have 11 unique and relevant riddles in their pocket (6 to field, 5 that they heard before and were asked here) success is inevitable. Pure attrition.
Addendum: Consider giving NPCs the chance to sacrifice resources of meaningful cost to lengthen the contest as well! If your players are eating up this riddle stuff and love a puzzle, give them even more of it and make it feel powerful by draining endurance, spell slots, stress bars, Ultima Points, whatever. Use rarely, or it won't feel dramatic is my suspicion.
Think about the cultural milieu and languages spoken by the NPC challenged. The only riddles they know are from those relevant cultural blocs or languages. This helps give the players a silver bullet- say the ancient lich doesn’t know goblin riddles, losing the contest to one of their crass, butt-centric riddles. This also makes learning about these creatures’ cultural backgrounds tactically valuable to identifying what riddles they might not know and so settle the dispute. If an NPC has a bespoke riddle for a contest that could not be encountered prior, leave a bunch of clues to encounter before the contest, like any other dungeon puzzle.
On that note, these cultures that make riddles have relationships and drama between them. If there is a war between men and goblins and you beat Clyde at a riddling game over the bar tab with a goblin riddle, it might put a sour taste in the mouth of him and the townsfolk. If you win the riddle contest with a riddle from outside the culture sphere of the people you’re riddling with, if they are unfriendly or uncomfortable with it, lower their personal/factional disposition by 1. If it is from a culture they are neutral or friendly toward, or one of their own riddles, no change to general disposition.
Now here’s a problem mirroring the attrition victory offered above. If the PCs know an amount of riddles pulled from a certain cultural bucket, the GM knows an amount equal or greater than that. How do the players actually win if those are the only riddles available and relevant in a given contest? I’m willing to say that at this point it’s come full circle to a test of wit. Both sides of the table are likely now initiated into this discursive form and are operating with a shared pool of metaphors. The players are incentivized to make their own riddles, or rephrase established ones. When a new riddle is introduced by a player, look at their backstory and/or known languages and attribute it to one of those blocs. If you know 3 riddles of a given culture distinct from your background, you are free to tag the riddles you make up as part of that culture.
I would also offer NPCs in a contest facing a new player-made riddle be provisioned 0-5 free guesses based on their abilities and to give the GM a sporting chance.
Addendum: Per the above, consider letting the NPC burn resources to get more free guesses, so players can feel clever! It's great gameplay feedback.
On the subject of improvised riddles, a simple principle I would go over with the table prior to digging a riddling-hole: Riddles are not lies or total nonsense. They reference actual events or objects that could be known even if it’s impossible to guess, like in a neck riddle. So encourage your players to aim for something not immersion breaking, but at the same time, run with it if it’s fun. We’re adults here.
But it does get at the heart of the messy social contract that makes riddling games work. It depends on trust in shared reality that, in a fantasy game, has room for impossible events that players can lean on for making neck riddles. Riddles are in some sense, for our purposes, in-jokes wrapped in a guessing game. TTRPGs are incubators for in-jokes, to the dismay of everyone else you know. It’s why I’m baffled that riddles seem difficult to render at the table, as it leans on the same muscle for managing shared metaphors that is in some sense constitutive of an imagination-based hobby.
To train myself, and my players, to handle this archaic form and channel that energy directly into the gameplay is why I’m opening a door for active riddling in my next elfgame. I already have ideas for expanding this loose system informed in part by the True Name rules over on Prismatic Wasteland. Time and luck will tell if I can jam it in to make riddles into spells. But until then, I'll see if I can find the joyful frustration in the GM chair. I give away an entire castle carte-blanche to the party after a long riddle chain, because one of the players looks me dead in the eye with a smug grin and asks, “What do I have in my pocket?”
Tax: Riddles, riddles for the crowd! Drink deep and be merry!
Four points to one tang
Without guard or hilt
A weapon drawn
After its quarry killed
What am I?
I roar without lungs
And churn no cream
Deep feelings seldom
As my surface seems
Support I all, yet respect I none
All tears flow into me as one
What am I?
A castle sans rampart or battlement
With sweet mortar laid by royal architects
What am I?
—
Works Referenced: Riddles: Perspectives on the Use, Function and Change in a Folklore Genre by Annikki Kaivola-Bregenhøj, published 2001