Puzzles, the riddle

Riddles are among the most common fantasy puzzles but good ones are hard to come by. Most are too well known and many of the rest are too hard. It is really easy to make a hard riddle by making it poorly. Nothing is more annoying that looking at a smug face who thinks they stumped you with a good riddle when in reality they wasted your time with a riddle that is impossible because it is crap. What follows is my route towards writing a (hopefully) good riddle.

Choose something definitive and concrete

In general I like to be able to see the object of my riddle because, ideally, your riddle will be describing it. Having no physicality makes this much harder. If you choose something like justice or the letter ‘e’ you’ll have to rely on quips and cues. Quips (“sometimes I’m blind”) tend to make riddles exceedingly obvious if they get the reference or impossible if they do not. Cues, like the placement of the letter ‘e’, are obvious if read and impossible if heard. No one seems to be impressed when you tricked them by orating a visual cue.

Choose something semi-unique

A swallow is definitive and concrete, but is too similar to other birds to describe. A riddle that has many correct answers should be scrapped and a better object chosen. Laziness on the part of the riddle maker shouldn’t be compensated for by just allowing more correct answers.

This isn’t to say that it can’t be similar to other objects, but within its domain it should stand alone. You should be able to describe the object in, at most, a few sentences and feel confident that someone would know exactly what you are describing. If you can’t do that deliberately, you’ll be hard pressed to do it in rhyme.

Choose something not-familiar

Being not-familiar is different from being unfamiliar. The alphorn is unfamiliar and makes a poor subject of a riddle. Lightning is too familiar and using it as the object of a riddle makes even a good riddle damn easy to solve. The ideal subject is not-familiar; something that everyone will immediately recognize but probably hasn’t thought about for a while.

Reimagine the object in a new way

A good riddle faithfully describes the object while painting a picture of something else. The goal of a good riddle is not to stump the guesser, but to make them slap their own face when you tell them the answer. They need to feel tricked, not beaten. The classics are the reimagining of the egg as a treasure chest holding the yolk or the life of man as the passage of a day. Importantly, the reimagining must also be definitive and concrete—the same pitfalls apply here.

Pick a narrative device

A good riddle has a narrative device that pulls the description through some progression. The common themes are temporal (birth-life-death), sequential (first I’m, then I’m, finally I’m), or linear (start, middle, end). The differences are often subtle, but they are important. For instance, sequential is better for discrete progressions whereas linear or temporal are better for continuous.

By way of example, you might wish to personify a river and reimagine it as a creature. A first person narrative riddle could begin with the creature describing its head (the head of the river), later its many limbs (the tributaries), and concluding with the hunger of his ever changing feet (a double reference to the shifting mouth of the river and a delta). In this sense, the progression linearly proceeds down the continuous stretch of the river.

A progression isn’t always required. A good alternative is to just solidly describe a single task, action, or behavior. For example, the following riddle doesn’t really progress (although you could argue it is sequential) but still tells something of a story. The important point is that there is a narrative and not a smattering of disjointed lines.

With armor born of a suit so old
I watch over a treasure of gold
Ever outnumbered, I shall not yield
And vigilantly tend the battlefield

Describe the “new way” with the narrative device

Describe the object as many ways as possible without giving the solution away. You want to be evocative, specific, and not superfluous. Each word should make the answer more obvious and even a single superfluous word can make the riddle feel unfair. You also shouldn’t intentionally ignore the dominant traits of the object; if the object is gold, the riddle should at least mention yellow.

When faced with multiple options, select words or phrases the pay homage to the object. This tends to dramatically increase the “face-slappiness” later when the answer is revealed. For instance, if “push” and “pulse” are equally viable when describing the Sisyphusian task of a heart, use “pulse” unless it gives too much away.

Make it flow

I think this is appropriately at the end. Better to have a good riddle that doesn’t rhyme than poetry that doesn’t mean a thing—at least if a riddle is what you’re after. Understand that someone will be speaking the riddle, whether out loud or in their head. Rhyming is desirable, but flow is more important. Try to match syllables and emphases so that when someone says it there is an easy rhythm. People tend to discredit a riddle that reads clunky (even if it is their fault) while one that flows is given more due consideration. It is fun to solve a riddle you like and annoying to toil over one you dislike; give yourself a leg up and start on the right foot.

This recent thread had many good riddles and a handful of my own—including one that still has no answer.