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How To Write the Perfect Riddle

It starts with Tolkien, for me.

You know that chapter where Bilbo finds the One True Ring, runs into Gollum, and the two have a riddle war?

It’s a masterful chapter, combining poetry, prose, and high drama; it sets up and presages the entire War of the Ring, all of Lord of the Rings. Then, climactically, Gollum offers this final riddle:

This thing all things devours:
Birds, beasts, trees, flowers;
Gnaws iron, bites steel;
Grinds hard stones to meal;
Slays king, ruins town,
And beats high mountain down.

That’s the kind of language that tends to bounce around your mind a little; to echo a bit. It’s the kind of language that is its own soundtrack. Slays king, ruins town, and beats high mountain down. You can already hear the beat.

(The answer, of course, is “time.”)

I’ve always loved language, particularly the English language, and my love of riddles and fantasy encompasses Tolkien, C.S. Lewis, H.G. Wells, and even Yoda, but it began as a kid with Dr. Seuss, our most prolific writer of perfectly metered language. All the Whos down in Whoville liked Christmas a lot…but the Grinch, who lived just north of Whoville, DID NOT.

One time I was thinking about an upcoming leap year, on a gray December day. February is the shortest month, even in leap years. Suddenly, a riddle came to me:

A dozen brothers in a ring
Among them dwells but one changeling
Though ever and anon he gains
The least of them he yet remains

I can’t explain it, but the entire riddle was just there one second. I recited it from my mind, grabbed a piece of paper, and wrote it down. Then I came up with another, and another. Over the next few months I’d write a riddle every couple days.

When my friends try to write riddles, they’ll start with an answer and work their way to the riddle. I think that’s how most people do it. I don’t, exactly – I’ll hear somebody talking about something, hear the characteristics of something, and I’ll realize that there’s a less obvious, more misleading way to describe that thing. Almost every great riddle is born on the fulcrum of a misleading metaphor.

I get inspiration from life and history – Netflix, books, bus stops, documentaries, post office runs.  I’ve found that riddling metaphor is rather like geometry, where three points define a plane. The riddle coming together is like a plane being defined. It comes together when three or more descriptive elements define its metaphorical plane.  After that, it’s more like writing music. Rhythm, rhyme, assonance, dissonance. Pentameter, tetrameter… so long as it’s got elegant meter.  A superior riddle must be in strong meter. That’s what provides the true narrative voice of the riddle for the reader.

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