Riddles seem to be underutilized in roleplaying games, at least the ones I’ve been present for as both a player and Game Master. The Riddle of the Sphinx to Oedipus, Samson’s Riddle to the Philistines (Judges 14:14 – 14:18), puzzles and word-games upon which the life of a hero balanced and the doom of the Philistines was set. Riddles need not be just the pun-ridden games of the Victorian nursery; ancient ciphers and cunning supernatural riddlers populate the yellowed pages of fantasy tales and legendry showing that great adventures are not just about exploration and action but also about solving riddles which can be adventures in and of themselves. Thusly, roleplaying sessions can be greatly enriched by the strategic use and shrewd construction of riddles by the Game Master. Riddles are a poetic mode of language of great antiquity not only meant to present a puzzle but also communicate a transformative perspective and carry a deeper meaning. A good riddle should be clear, fair, present a challenge to its audience, and have somewhat of an aesthetic appeal as well as having an element of engagement that draws its listeners in like moths to a flame.
A riddle is a short composition posing a question where the object of the riddle is to obfuscate the question itself forcing the listener (the riddlee) to decipher the question and in the deciphering the answer is reached through the clues discovered within the riddle. “The riddle is a short lyric poem that poses a question, the answer to which lies hidden in hints.” [Turco, Luis. 1986. The New Book of Forms: A Handbook of Poetics. Expanded ed. Hanover, NH: New England University Press. pg.134]. Apart from any strict structural definition of a riddle it’s the context that makes an expression with descriptive elements, whether written or verbal, into the question part of the riddle. A riddle presents its clues in a roundabout way or with an altered perspective and poses its question. These few and simple parts allow riddles to take on a wide variety of structures from lyrical poetry, songs, simple rhymes, short stories, as well as seemingly straight forward questions in non-poetic language. It is the context in which the riddle asks its question which is of importance. The clues set up in the riddle can imply the answer or yet another clue depending on their juxtaposition to the question part of the riddle.
The riddle can be thought to exist in its own world constructed by the riddler and explored by the riddle – very applicable to fantasy roleplaying indeed. The use of language in a different or unfamiliar way within the riddle itself can alter the initial impressions not just muddying the clarity of the statement or question but providing a completely bizarre and alien picture that appears to be something entirely different until its mysteries are penetrated and the machinery of the riddle is exposed. The Riddlee’s task is to turn the unfamiliar world of the riddle into the familiar. “The way in which the riddlee arrives at the riddle’s answer involves understanding the relationship of the parts of the riddle and grasping a new ordering of things, and along with it the meaning of the riddle.” [Montfort, Nick. 2003. Twisty Little Passages: An Approach to Interactive Fiction. The MIT Press. pg.50] Merely stating the answer to the riddle is not enough for the solution. The riddlee that has truly reached the solution must be able to completely explain the riddle-question and how each of the clues operates. To be fully solved the Riddlee must solve the riddle announcing the solution, and explain the riddler’s intent with reference to the clues. As it is the riddlee’s role to solve the riddle it is the riddler’s role to construct their riddle fairly and present it with clarity.
A riddle must express itself clearly enough to be solved, obliquely enough to be challenging, and beautifully enough to be compelling (Montfort). A riddle presents something familiar in a transformative and unfamiliar way, if the riddle concerns something that is unknown to the riddlee then it becomes unsolvable. A riddle communicates the known and is ineffective in carrying information about the unknown to the uninitiated. Take the Sphinx’s riddle for example which asks (what follows is a popular modern version, there are several different versions of this riddle), “What is the creature that walks on four legs in the morning, two legs at noon, and three in the evening?” The answer given by Oedipus was “Man”. The question the monster posed was itself obscured by substituting the major phases of a human life (infancy, adulthood, and advanced-age) with another unit of time often poetically associated with those phases (morning, noon, and night) but still allowing them to serve as clues leading to the answer for one who can figure out how to look at the riddle when an infant one crawls (walking on four legs in the morning), when an adult one walks on two legs, and the third leg in old age would be a cane. This last clue changing the number of legs to three pulls double duty not only performing as a clue but also narrowing the potential answer as well probably confusing the unfortunates which the Sphinx strangled and ate. Though difficult the Sphinx’s riddle is a fair riddle, the hardest part of composing a riddle is making sure that it’s fair. Good riddles rely on description and metaphor with absolute clarity of meaning being reserved only for the solution and the presentation of the language of the riddle. The easier it is for the riddlee to understand the language of the riddle the more they can be assured that the riddle is fair. Of course, such aspects of the riddle as required prior knowledge, the more the riddle is a logic puzzle the less the riddler has to rely on the riddlees’ knowledge but the riddle may become overly genericized as a result, and difficulty should be taken into account. The riddler must construct their riddle fairly that is fair in the metaphorical clues provided within the riddle itself in relation to the riddlee. A riddle without clues or with those insufficient to lead to the answer is unfair even if its language is easily understood.
To pass into the city of Thebes, Oedipus had to answer the Sphinx’s riddle which presented an obstacle in the narrative for the hero to overcome but with cunning rather than shear brawn. In that mode the Sphinx rather than presenting itself as a classic sword & sorcery monster, takes up the position of what is known as a Guardian of the Threshold. “Generally, any GUARDIAN OF THE THRESHOLD is likely to require the answer to a riddle.” [Clute & Grant. 1997. The Encyclopedia of Fantasy. New York, St. Martin’s Press. Riddles] Samson’s riddle to the Philistines, however, is a great example of a bad riddle specifically an unfair one. His riddle, “Out of the eater, something to eat; out of the strong, something sweet”, has clues within it but the greatest clue the one required by the riddlee, in this case the Philistines, to know in order to solve it is not present in the riddle itself. It’s unfair to those lacking Samson’s life perspective basically it’s unfair to everyone except Samson himself (and the reader of the tale). The answer is the honey he had taken from the honey-combs that he found in the body of a lion that he had slain (Judges 14:6) after he had passed back by its corpse later. He never let anyone else know from where he had obtained the honey. His riddle is contextually unfair. Of course, within the context of the tale the purpose of the riddle was more of a pretense for other events, it’s more of a literary device in service of the tale its quality is not of any actual importance within the narrative. Another well-known and very unfair riddle of almost an identical nature is that of Rumpelstiltskin’s which is meant to be unsolvable by the story’s heroine, giving her three days to guess his name. Another example of an unfair riddle is the Mad Hatter’s riddle asked of Alice, “when is a raven like a writing desk”, he admittedly didn’t know the answer to his own riddle. Of course, all three of these examples of the unfair riddle served other purposes within the narratives of which they are a part. The riddle of the Sphinx is a fair riddle but is also a part of a greater narrative relating to the previous unfair three to which the riddlee displayed his cunning by presenting the answer and the explanation of the question. In a roleplaying session riddles NEED to be fair to the players; of course if the player characters are posing a riddle then of course it will not carry that requirement.
When it comes to the roleplaying tabletop, riddles can add to the RP element of a game engaging the players and encouraging teamwork when attempting to solve it. Riddles can help to add an air of mystery to a game session as well as deepening the world setting. The riddle itself should have reason to exist and take elements from the setting in which it and the characters exist firmly imbedding it in the game world. The riddle should be crafted to avoid modern/real-world knowledge that is not present in the game world. Essentially what works for a newspaper puzzle is probably not going to work within the game world. A riddle posed by the GM should be incorporated into the adventure in a manner that emphasizes its importance such as needing to answer a riddle to open a riddle-door behind which a serious goal is hidden, pass a Threshold Guardian that the players can’t otherwise just beat-down, or occur at a critical point in the communal narrative of the campaign. Any puzzle, not just riddles, needs to feel like an important part of an adventure, not a simple barrier that can prevent the players from enjoying the game. Not every riddle needs to be a work of poetry or even entirely original when used within the context of a roleplaying session but the Game Master as the riddler must keep fairness and clarity in mind as well as figuring out how to engage the players. The riddle itself needs to be engaging and hold the players’ (and thusly the characters’) attentions. The riddle needs a reason to exist and a purpose there should also be a reason that the players actually want to solve it. Giving players at least an implied benefit and/or penalty if they do or don’t solve the riddle even if it’s just to propel an important plot point or trigger and event helps to engage them. They should have some sort of an idea of the consequences of either success or failure perhaps both and if they have a choice the implications of accepting the challenge.
Riddles can be constructed rather quickly by GM’s in their basest form in a few simple steps. First, think of an object (the answer), think about how to describe that object (specifically the vocabulary involved which will both obfuscate and carry the clues), and once you finish that you need to think of ways to tell your players this in a less obvious but more interesting way (this is where phrasing and any literary devices can be applied), then try to put together the riddle in such a way that’s interesting but also clear in that the riddlees will be able to understand the riddle itself keeping the clues in mind. Working backward from the answer makes sure that your riddle has a definite answer. Also check to make sure that the riddle is fair, the players should have the knowledge that will allow them to not only find the clues but also to process them to formulate the answer. When dealing with groups, then the tidbits of required knowledge can be distributed among the individual players forcing them to work as a group to solve the riddle. Note also the use of riddles should also be minded by the GM based not only on the nature of the group and what they may enjoy about the roleplaying experience but also the commonality of a riddle and its importance to the game. Not just a reward behind a riddle-door or the attainment of access from the Guardian of the Threshold but as a device that can add to the depth of the fantasy world and have consequences in the answering. Rarity is also a factor; if riddles are fairly common then they become less valuable as a roleplaying device the use of riddles as simple obstructions in a dungeon cheapens them likening them to the typical traps found in such a place.
The ancient art of riddling can add a certain mysterious depth to a roleplaying setting as well as adding a little cerebral fun to a game session lending a little diversity to the exploration, action, and strategic aspects of the game while also encompassing all of those ideas at the same time.