When I write short stories, I love experimenting with fantasy tropes such as dragons, trolls, and prophesies. Though they may seem trite, I like to see if I can do anything with them that has not been done before: play with them; flip them upside down; personalize them; use them as metaphors that represent psychological truths.

One of those fantasy elements, which I see over and over, is riddles. Among the most famous are the riddles Gollum gives Bilbo Baggins in in The Hobbit. They are clever and even poetic.

Voiceless it cries.

Wingless flutters.

Toothless bites.

Mouthless mutters.

(Answer: wind)

J.R.R. Tolkien was not the only one to use riddles. J.K. Rowling used one for the climax in the Harry Potter series: “I open at the close,” referring to an enchanted Snitch that would only open once Harry was willing to die. And Stephen King used riddles extensively in The Dark Tower series in his confrontation with a smart-mouthed, evil train.

Why do fantasy writers like using riddles in their fiction? What is their appeal? Why are monsters and trolls constantly challenging heroes to battles of wits? Maybe it is partly because, if you are fighting a magical entity immune to fisticuffs such as a ghost, a demon, or The Grim Reaper, you are not going to win with a swift uppercut to the jaw. A different kind of battle, a more cunning one, is needed.

Also, riddles engage readers by making them part of the struggle against an enemy. If the reader gets the riddle right along with the hero, he shares in the feeling of triumph. But why are riddles such an entrenched tradition in the fantasy genre specifically?

I did some research on riddles. After answering some of them, I am beginning to understand why monsters and fantasy writers like them so much. They challenge both the intellect and the imagination; they imbue the world with mystery and magic; they make common objects irresistibly strange.

An example: The more you take of me, the more of me you leave behind. What am I? It sounds like something that could only exist in another universe. To solve it, my first impulse is to try to think of some item I can grab and stuff in my pocket, something that would magically replenish itself tenfold as I stepped away.

Of course, that is logically impossible. The puzzle depends on a quirk of the English language that turns the ordinary answer, which is “footsteps,” into something more than itself; the riddle propels footsteps into the world of magic.

At the same time, the puzzle brings attention to the odd expression “take footsteps.” The expression makes no sense at all when you analyze it. No one reaches down and takes footsteps by hand; if anything we make them. But for a moment the riddle leads you imagine that somewhere in the universe there is an object that magically replenishes itself after you take it.

Riddles are perfect for the fantasy genre because, through linguistic slight of hand, they transform boringly common objects into mysteries. The common practice of phrasing riddles in self-contradictory terms makes the answers seem as if they could not possibly exist in a universe built on orderly laws of cause and effect. Some examples:

How can a pants pocket be empty and still have something in it?

What word becomes shorter when you add to letter to it?

What has four eyes but cannot see?

What has hands but cannot clap?

In case anyone wants to solve them, I left out the answers, but these are all classic riddles, so you can find the answers quickly on Google. My point is that many riddles depend on contradictory phrasing, but the contradictions are illusions; usually they depend on a linguistic knot.

What goes up and down without moving? When I first heard this riddle, my mind went in two opposite directions at once. I imagined things that move and things that are absolutely still, and tried to reconcile them into one object, which is impossible.

The correct answer is “a staircase.” There is no contradiction, because a staircase does not really go up or down; it does not go anywhere at all. It is just a hunk of material constructed in a certain way. We say that a staircase goes up or down only because of how we use it, but the inaccurate expression was like a wand that enchanted the staircase.

These observations of how riddles work are new to me because, until recently, I have never given them much thought. But after having fun with them and getting stumped by them, my opinion of them had improved. Riddles enchant common objects; they probe into the nature of death, time, fate, and nothingness. They awaken a sense of wonder that makes you feel like you are encountering a common object or idea for the first time.

Riddles require a different way of thinking. They celebrate paradoxes. They employ ingenious metaphors. They frustrate. They illuminate. They misdirect. And solving a challenging riddle comes with a soaring sense of triumph.

As a fantasy writer and unapologetic nerd, I decided that I should be able to write riddles as well as J.K. Rowling, so for practice I made one up. “As I sit, I go far. To tell truth, I lie. With a touch of my fingers, I make dragons fly.” As far as I know, there are not any other riddles about fantasy writers, but if any of you can think of any, let me know.

There are more practical reasons to write riddles than building nerd cred: In case the Grim Reaper ever comes to my doorstep in a sporting mood, it is not a bad idea to be prepared. I will have a far better chance of winning a battle of wits with Death if my riddles are not ones he has heard before, and, like any self-respecting metaphysical entity, he is bound to have read The Hobbit.

Maybe if my riddles are clever and challenging enough, I can keep Death afraid of me. Or better yet, he will become so addicted to my riddles, he will want to keep me alive. Or, best case scenario: he and I will become so chummy, he will read my books and write reviews of them on Amazon. Favorable ones, I hope. I hear death has a lot of clout in the literary world – both here and beyond.

If you enjoyed this post you might like my other writing. Take a moment and sign up for my free starter library. Click here. Also my new novel “The Ghosts of Chimera” will soon be published by the folks over at Rooster and Pig Publishing.