My players love riddles too, and I've found that making deep and fantastic riddles isn't as difficult as you might think. After all, as the DM there's no need to be completely original, and as they say the internet is your best friend.
Three steps to creating a deep riddle for your RPG games:
1: Grab an average riddle.
2: Find rhyming words that are appropriate and create the verses along the way.
3: Put it all together.Let me explain in further detail:
1: Grab the riddle: Personally, I simply use " riddles.com " , they've got a bunch of riddles, more than you'd ever need at least.
Go to List of Riddles and grab the first or fifth that looks interesting. For this example: I found this one.
What is it that is deaf, dumb and blind and always tells the truth?
A mirror.This is a good basic outline for our riddle. The answer will be "A mirror" and the hints will be that it is "deaf, dumb and blind" and that it "always tells the truth"
I will have one verse for each hint in the riddle, so I already have an idea of how I want to structure the riddle.
Verse 1: something about deafness
Verse 2: something about dumbness
Verse 3: something about blindness
Verse 4: something about always telling the truth
2: Find rhyming words that are appropriate and create the verses along the way.Let's face it, riddles that rhyme are pretty damn mysterious. They have that fantasy element to them, when compared to just your average riddles. So add that to your riddle. Whether it’s the ABAB, the AABB, or the ABBA rhyming scheme, that’s your choice. I’ll simply use AABB for this example.
Don’t feel restrained in proper grammar. Talk like Yoda, you can. More of a fantasy element, it adds. More wise, the words sound. (Ok, I’ll stop now.)
Now, another fantastic element for riddles can be repetition. For this example, I will use "It is I" at the beginning of each verse, except perhaps the last one or the last two. We’ll see how that works out.
Find a rhyme dictionary. I use " rhymezone.com " simply because it was the first result on Google.
So, I want to make my rhyming words make sense when compared to the source riddle. For this example, the first verse is going to relate to deafness. So, I will use a word that is related to that, sound. The rhyming search engine gives me a bunch of good words that would rhyme with sound, so I decide to stick with sound.
It is I, who cannot hear any sound,One of the words that rhyme with sound is astound, which could be the opposite of “dumb”. So, I’ll use that, keeping a repetition of “It is I”
It is I, who has no mind to astound,Now, this sounds very strange, but this is simply a rough outline of what I want, so let’s move on to the next verse. “Blind” is a word that has quite a few rhyming words, so I’ll simply use it.
It is I, who is completely blindA word that rhymes with blind is find. I could use that as in “finding the truth” or something. So I will.
And yet the truth with me you’ll always find.3: Put it all togetherIt is I, who cannot hear any sound,
It is I, with no mind to astound.
It is I, who is completely blind
And yet the truth with me you’ll always find.
Who am I?And there you have it, you have created a riddle. Now that you have it done, you can change the wording or replace some words.
Hope this helps. And sorry if the guide is a bit confusing, it’s quite late at night and I can barely think in a coherent fashion.