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Riddle Me This:
The Art of Writing Riddles

By Brendan Arnold

A great way to add spice and flavour to your campaign is to include a riddle. While this is most true for fantasy, a good riddle can work in other genres too, such as horror or even SF, and characters who talk in riddles are great entertainment in any story. What's more, riddles are a great way to give your players a puzzle that engages their intelligence and imagination at once. They have to use their brains, rather than just rolling for it, but if the riddle is good, it won't detract from the story and make the players think they are back in school.

Riddles are something that I personally do not find difficult to create. I am aware, however, that many other people have difficulty in creating riddles and other word tricks with which old sages or talking doors can confound PCs. In this article I will outline the techniques that I use for designing such wonders. If you are not familiar with some of the more complex terms used, don't fret! Many are things that you probably already know but have been given long names and are only used in this article for clarity.

Start with the answer

Firstly, I find riddles much easier to make if you first start with the answer. Always choose something appropriate to the situation. For example, if you are just a few feet away from total divine power and the answer to the man at the gates of heaven's riddle is something like 'potato' then it kind of destroys the moment! For most of the examples in this article I will demonstrate techniques with the answer 'dark'.

The Techniques

Most riddles I find use certain literary techniques to trick the listener's ear. Below is a list and applications of the ones that I have encountered.

  • Semantic Field: A good start is to find a group of words which are associated with your answer. For the example 'dark' we could extract, black, blackness, void, fear, light, evil, confusion, veiled, blind, shadow. These words can then be used within the riddle to hint at the answer.
  • Metaphor and Simile: Many riddles use metaphor to mislead and distract the listener from the real meaning. Metaphor is comparing the solution of the riddle with something else which is unrelated, for example 'I snuff the day' compares the darkness to a 'candle snuffer'. Simile is even more common than metaphor, when a direct comparison is used. How many times have you seen phrases like 'cold as ice' and 'hard as stone'. To find a suitable comparison, think of some of the properties found within your answer's semantic field and choose one to compare. For my example of 'dark' I could pick out it's blackness and say something like, 'as black as coal' or for 'void' I could say 'as empty as space'.
  • Metonymy: Similar to metaphor it is the substituting of the word for something which it is a part of, or something which is a part of it. Some examples are 'smokes' for cigarettes and 'the law' for the police, A lesser constituent of dark could be 'shadow' and a greater constituent could be 'void' so substituting them instead of the answer would give something like, 'I am shadow, I am void'.
  • Synonym: This being different word or phrase of similar meaning (very few words, if any, have exactly the same meaning in every context). Synonyms of dark could be 'without light', or 'blackness,' These can be used in the riddle to hint at the solution. Thesaurus are full of synonyms and most word processors will provide a built-in thesaurus.
  • Rhyme: I know that most riddles rhyme as a whole but there are other ways in which you could use rhyme to confound by including a word that rhymes with the answer. This little used technique can be used to great effect. For example if I said 'I am similar to lark' for our example of 'dark', most people think about the bird rather than the word itself thus throwing even especially clever players off the scent.
  • Onomatopoeia: A technique that is also little used, this involves making the words sound like the noun they are describing. This is a difficult one to apply to 'dark' since dark has no noise, but for example if your chosen answer was 'a snake' then you could lengthen any 's' sounds when reading the riddle out to sound like 'hissing'.
  • Literal Thinking: Remember the old 'what was the drivers name' question? The Answer, of course being, 'What' - it was a statement not a question. This technique often works well with clichés (well known and overused phrases.) Taking our example of dark and altering it a bit, 'I am as black as coal, what am I?'; the answer being 'coal'. This works well because it is a cliché.The following wouldn't work so well: 'I am as black as dark, what am I?' the answer being 'dark', because it seems like an odd thing to say. The last phrase is not a well known cliché and so arouses suspicion as to why you chose those words, making the literal thinking a bit too obvious.
  • Personification: By describing the word in question with 'human' characteristics you can imply the answer but also add another dimension to what the listener imagines the answer to be. This is best demonstrated by an example: 'I shy away from my foe, the sun', not literally possible of course but it conjures images of a dark warrior being defeated by the sun. This is a technique which is used an awful lot in riddles, (the common use of 'what am I?' is of course a personification of the answer.) Which brings us nicely onto:
  • Opposites: Another way to add a clue as to what the answer might be without actually telling it straight out is to use opposites. Also if you make the entire riddle so that all clues point to the opposite of the answer then include a line that implies that the opposite to your conclusion is your answer, then it adds another stage to the solving process. For example, if I were to use the opposite of 'dark' which is 'light' then the riddle could go something like this. 'Of the suns rays, I am born, I live in beacons and guide many through storms, yet it is not with me that your answer lies, it is my foe the one I despise.'
  • Cliché and Collocation: A cliché is a piece of language that has lost its impact through overuse, like the old 'why did the chicken cross the road' joke. They are usually looked down upon in most creative writing, but in riddles they are abundant and very useful because of their familiarity. Many riddles include incomplete clichés with the missing word being the answer. In this form, simply because it is a cliché does not mean it has to be obvious. For example, take a look at the following (very well written,) riddle quoted by 'Polaris.'

    What does man love more than life,
    Hate more than death, or mortal strife?
    That which contented men desire,
    The poor have, the rich require?
    The miser spends, the spendthrift saves,
    And all men carry to their graves?

    The answer is 'nothing'. This becomes obvious when we consider each of the questions individually, man loves nothing more than life, man fears nothing more than death, the poor have nothing whilst the rich have everything (and so require nothing.) 'Nothing' is so often used in such phrases it becomes possible to complete the sentence by guessing at the missing word. provides a searchable archive of clichés. Entering the example answer 'dark' into the search box, it comes back with many results. Here is a selection of the most appropriate (i.e. the most commonly understood ones). For those that have never heard of the cliché I have included what they mean in brackets. Note that when creating you own riddles be sure to use references that you and you players will likely know.

    • dark horse (a secretive person)
    • a shot in the dark (a wild guess)
    • to keep someone in the dark (to not let someone know about something)

    One way to integrate clichés into riddles is to replace the answer with a pronoun such as 'me' or 'I' (if you would like to personify the answer,) or 'it'. For example:

    'A shot in me is a long shot indeed,
    Keeping someone in me makes for a secretive creed.'

    Another way is as in the 'nothing' riddle above, where it asks questions using the cliché as a clue. For example:

    'What makes a horse, one of secrets?
    What makes a shot one of uncertainty?'

    A collocation is similar to a cliché but usually includes only two words that just seem to go together well. For example 'Big Mac', or 'Compact Disk'. These can be used in similar ways as clichés, by substituting the answer with a pronoun or making it into a question.

The techniques above work for both written and spoken riddles. Here are a couple more that would work best only for written ones (i.e. on a player handout).
  • Acrostic: perhaps you remember being asked to write a poem by a junior school teacher where each of the first letters of each line spelt out a word. For these, hints must be given within the poem to suggest this, otherwise it's unlikely the players would ever think of looking. An example for dark is below:

    Duels of good and evil,
    A fighter of good am I,
    Revealed beside watched words,
    King of the black night sky.

    You can see the word 'dark' spelt out along the side fairly plainly. Here I emphasised them with capital letters; obviously you can make them as plain or as subtle as you like with emboldening, capitals or other forms of highlighting.

  • Anagrams. Taking the letters of a word and jumbling them up to make new words, anagrams make great riddle clues. It can be difficult, however, and sometimes impossible, to make a new word from your clue (as is the case with 'dark') especially if the answer is few in letters. Browsing the web, I came across a great site for generating anagrams. If you plan to use anagrams, it may be worth extending the answer into a phrase so as to gain better results when using the generator. Changing 'dark' to 'confusion', I gained 'focus in on' as an anagram. Once again, you will need some kind of a clue that the solution is an anagram. In this example, the second line gives such a clue. To help disguise the rather strange sounding line 'focus in on', I have placed it at the end of the verse. Many poems place their 'cryptic' lines at the end, leaving the reader with something to think about and so it seems less out of place to have our anagram here.

    Caused through inorder,
    Currently out of order,
    'focus in on'

    I'm sure you could think of much better ones given time but hopefully you have the general idea.

Making it Sound Good

It is a good idea to make the riddle sound catchy and poetic. This gives it resonance and charm and brings it to life so that players will remember it. No one will remember a riddle like 'I am similar to a lark, I'm blackness'. So once you have all the clever bit sorted out, you need to dress it up a bit. The above literary techniques and the following below can help make a truly memorable riddle.

  • Alliteration, Assonance and Consonance: Alliteration and assonance is when sounds are repeated in subsequent words. Alliteration is when this is the first syllable of a word, assonance is when it is the vowel sound in a word or syllable (but not necessarily a rhyme – eg look and wood). Just like rhyme, this repetition of sounds sticks in people's memories and can provide a certain element of light heartedness to the riddle as well as adding emphasis. Consonance is when words have the same consonants but different vowels; the effect is again similar to rhyme. The following riddle uses consonance rather than rhyme: 'Black as black but like a lark, The shrouding sheet for those that lurk.'
  • Parallel Phrasing: This is simply where the same words or patterns are repeated at intervals. For example, 'I'm like a lark, I'm as black as black'
  • Balanced sentences: Giving each sentence or clause a similar length and amount of syllables, this can allow for riddles that sound 'well rounded' and cohesive. The above example is a balanced sentence whereas 'I am similar to a lark, I'm blackness' is not balanced.
  • Rhyme: This is the best technique of all for sounding good and being memorable. Rhymes catch the ear and the imagination more than anything and are very powerful. They can be difficult to integrate into your riddle if you aren't the poetic type, but with effort they are not impossible and can make it really worthwhile. The "nothing" example above is a good example of this.

Getting Sentences To Fit

If you have trouble getting your riddle to fit into verses or using the above techniques then try firstly altering the semantics (word order). Many sentences can be written in more than one way and often the 'non standard' word order sounds the most archaic or poetic (see the third line of the example below).

'I am a fighter of good.'
'A fighter of good am I.'
'I am, of good, a fighter.'

Without going into too much detail, it is simply a matter of splitting the sentence into chunks where the words are related ('of good', 'a fighter') then rearrange them. If they make sense then a new sentence is born. Note: be careful that the meaning is still appropriate, as this may change dramatically with the altered order. If the sentence length is the problem then extensive elipsis (the removing of 'non-essential' words), can help. It is not necessarily long sentences that convey a 'mythic' feel. After all, medieval people, for example, were largely illiterate. You may be surprised at just how much in a sentence can be omitted. For example the above sentence without ellipsis should actually say,

'I am a fighter who fights against goodness in people'

The best way to cut down a sentence, again without going into a lot of detail, is to just use common sense. Ask yourself, 'What have I already established earlier or what will I establish later in the riddle? Do I need to state it again in this line? Am I stating the obvious?' and most importantly 'Would meaning be lost if I missed out this particular word?'

Of course, your sentence may be too short. The good news is that people often write with out even knowing they are missing words out. Thus, simply identifying what is missing and adding them in should make the sentence longer. We demonstrated that above.

You should find that getting a sentence to fit into acrostics, parallel phrasing, rhymes and others a whole lot easier using ellipsis and altering semantics.

"Letter" Riddles

Certain types of words for answers require different ways of thinking for the 'solver'. An interesting example of the answer changing the thinking process need to solve the clue is 'letter riddles'. Here the answer is a letter of the alphabet and all the clues imply that the answer lies within the object being described rather than in the word for that object. An example for the letter 'e' is below

The Begining of Energy
The end of time and space
The start of Entropy
And the begining of every end.

and this one for the letter 'v'

With Thieves I Consort
With the Vilest in Short
And Savants Cannot Lose Me
For I Am The Center of Gravity

Before I start to analyse this I should warn you that the language starts to get a little technical here.

The two examples above rely largely on cliché and collocations of a certain type, specifically those that include or have had a preposition somewhere in the sentence. For those of you who've forgotten your primary school grammar lessons, don't panic: a preposition is simply a word that states location or condition relative to something else. Examples of common prepositions are in, on, under, within, over, from, to, outside, inside, with, at, and through.

The reason why the above riddles don't seem to have many of these words is because of elipsis (the ommiting of 'unneccesary' words.) Look at the first example. The preposition 'At' can be placed at the start of the first three lines, and as the second word in the forth line, but the author of the riddle has decided that 'at' was an unneccessary word and missed it out so that the lines were more balanced in length (as well a neat example of parallel phrasing). The good thing about these riddles is that you can really use any cliché which uses a preposition (and the letter of choice, of course), because the preposition will point to the letter. The same goes for collocations.


Finally after you have created your riddle, it is vital to test it on someone. Even if you think that it is blindingly obvious what the answer is, still test it out. It is surprising how differently people think. There is nothing more disheartening than to create a riddle and then to see your party solve it in seconds or spend hours and hours puzzling over it until you have to give them the answer yourself. Getting the balance right here is never easy – the only way to do it is to know your players, and to keep practicing.

Thanks for reading and I hope that this will prove beneficial in producing some great riddles for your games.

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