How to write a riddle

Published August 21, 2009 by Eli Stutz

As you may be aware, one of my long time hobbies is writing riddles. Not the joke kind (I wish those two things had separate words), rather the kind where you have to guess the answer. As in Samson, Oedipus, Bilbo Baggins, etc. I began coming up with them after playing the Sierra adventure game Conquest of Camelot in 11th grade – that game had a scene where you needed to answer riddles in order to pass – and they had quite a lot of decent ones. I figured I could do the same. Sixteen years and ~300 riddles later, I’m just about ready to give you some tips on how to do it yourself. So here goes, here’s my big secret:

1. Think of a answer.

That’s right, the answer comes first. It can be a lot of things, but it can’t be anything. You can’t pick something that most people don’t know about. It’s got to be something that’s common knowledge. It can be very simple, like: the moon, a cat, a frog, etc., or it could be one level more advanced like: toothpaste, dice, a deck of cards, etc. If it’s something like: oxygen, a black hole, an eclipse, ravioli – then be aware that some of your younger riddle guessers may be excluded.

2. Think of clues.

Write down several aspects of the answer which could be hinted at by clues. It could be the color, what you do with this thing, it’s parts, etc. Start writing down short phrases which illustrate each clue. If possible, and this is more advanced, try to see if these phrases can somehow be logically connected to each other in order to form some kind of a thought. Here’s an example:

The answer is: a battery.

The riddle is:

I lie still in the dark,

In my tight little bed,

Where I work ’til I’ve died,

With a bump on my head,

And that’s just my positive side!

What am I?

Each of the lines above describes some aspect/behavior/appearance/parts of a battery, but they have been linked into one idea: something which has unfortunate living circumstances. That’s the “disguise” of the answer, which makes for the appeal of a great riddle. It sounds like something else, and then when you find out the answer you see how you were “tricked” by the clever disguise.

3. Rhyming and rhythm.

Rhyming is not mandatory, but I prefer it immensely. Try to get you lines to rhyme (it could be abab, aabb, or even aaab structure), since this will add to the appeal and poetry of the riddle. I give almost as much importance to how the riddle sounds poetically as to the content itself.

Try to concentrate on poetic rhythm as well. The flow of the lines should “sound good” and fit together. This may be easier of some of you than others. It may have to do with a musical sense.

4. Polish and tweak

Now that you have the lines down, try tweaking some of the words, play around with them a bit for greatest effect. You may do some rewriting at this stage until you have a finished product that you like.

5. Test it out

Find some friends and family and try your riddle out. See how long it takes for them to either get it or give up. When you give them the answer, do they say “Oh, that was good!” or do they start objecting. No riddle is perfect, but some come close, and the mark of a good riddle is that “Oh!”. The best riddles are those that take most people time to get. Too easy or too hard is not what you’re aiming for, and of course there will be a range, depending on each riddle, and on each person you ask.

All in all, I find riddle writing fun – a great creative outlet. And my audience enjoys them as well – a win-win experience. And they’re short, so you can knock them off in as quick as half an hour, once you get the hang of it.

Happy riddle writing!



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