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RPG Riddles: The Good, Bad and The Ugly
By Valdor19 Posted in (DND) Dungeons & Dragons, Blog on August 26, 2020 0 Comments 8 min read
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As your party turns the corner they are able to see the fruits of their labor in front of them. The door that will lead them to the ancient treasure vault of the dwarven kings. Cautiously, you all press forward knowing that there are still dangers. Suddenly, in front of you, a grand creature appears. It’s large lion body coils in muscle and it’s wings spread wide across the hall to bar your entry. You whisper to yourself under your breath as only you have the knowledge to know that this beast is a sphinx, guardians that are set in place to not only test invaders physical strength but their mental capabilities as well. The Sphinx looks down at your meager group of four and in a booming voice says, 

“I am no bird, despite my feathers
So leave your cage, leash or tethers.
Yet I fly from perch to heart, 
Let loose to the sky by my counterpart.
I am no tree, despite my wood,
So your axe here will do no good,
To protect yourself from my affection,
You’ll need something with more reflection.
I am no sword despite my steel,
So away with your brutish warrior’s zeal,
I command my form with much more grace,
While still delivering death’s embrace.”

You know this. In your travels deep into arcane mysteries, you know the answer.
But before the solution can come to you, the dolt barbarian you just picked up answers, “an arrow”.

    Riddles in literature have been around since the earliest days of storytelling up to the most recent times in books and movies. Nothing displays riddles better than the fantasy genre. Heroes of all types strive to solve these puzzles to further their goals and to pursue the objective of adventure. The challenge can show the growth of a character in their wits and intelligence while moving the story along. From the Sphinx in Harry Potter and the Goblet of Fire to The Hobbit‘s riddle challenge between Gollum and Bilbo, these characters triumph over their adversary. The one medium where these riddles don’t appear to harmonize is in tabletop RPGs. More specifically, Pathfinder and D&D.

    In the many years I’ve been gaming with my group, we’ve encountered countless riddles. I tended to get disinterested for that section of the game and feel as if it was a waste of time. My fellow group members had also expressed frustration. Not because the riddles are too hard, but because it takes us away from the game and turns it into a time consuming mini-game. 

    The first reason why I dislike riddles is because it takes me out of character. When I am playing, I really try to become who my character is, and now I am being asked a question that my character might not know, but I am supposed to give an answer to this as myself? The riddle is supposed to be an in game challenge for my character so why am I being challenged as a player. This really tends to break the narrative of the story. Keep the game in the game!

    Now I want to discuss the difficulty of these in game puzzles. Nothing annoys me more than the whole group being stumped on a riddle just to have the GM parrot over and over again, “this is easier than you think everyone”. I am glad they think so, but the party has been here for 30 minutes trying to come up with an answer. Riddles are weird like that. They are supposed to be tough until you know the answer. After it has been solved, then it usually makes sense and you wonder why you didn’t know it before. You and your party now face the end of your game time, but you have just spent a majority of your efforts to solve this enigma.

    The final reason is the biggest one. Riddles and word play tend to add nothing to the narrative. When you take the riddle out of the game and are challenging the players instead of the characters, now adding a challenge with no real downside for failing. With unlimited guesses for the group, we will eventually figure it out, it might take a while, but we will get it. So we just answered wrong? Well, nothing happens, guess we try again. And again. And again… Until we just wasted 2 hours, (yes it really took us that long in a game one time and the puzzle was required to continue the story). When in the end we could have just done something else to achieve our goal in a more engaging way. 

    With the way riddles are typically done normally in question/answer format, I find them ineffective in a game. That’s not to say that we still can’t use riddles. It can be done in ways that hopefully circumvent or at least lesson the issues I pointed out earlier. I will outline a few ways I have thought to do this. There will be more creative avenues we could take, but these are a few of my ideas.

    Let us first look at ways to pull the whole issue back into the game so it still feels like our character is at least working through the challenge. Find the highest Intelligence and/or Wisdom modifier of the characters in the group or even combine everyone’s highest mental stat. Use these as a way to give hints of some sort to narrow down the answer for each bonus modifier. You can even allow the group to ask a question to try to eliminate false answers or get clarity on the more obscure parts of the riddle. Now your characters are still assisting in trying to solve an out of game puzzle and hopefully cutting down on discussions. 

    This next suggestion will make the riddle now a full game mechanic and put 100% of the puzzle onto the characters. Simply look at a riddle and put a DC to it. From a super simple riddle meant for kids to a riddle that has stumped acolytes for centuries, the riddle can just be assigned a mechanical difficulty and allow the players to roll for it. We should obviously make the riddle and DC level appropriate the current party but change it up to suit your purposes. This may seem boring to those that actually love the riddles, but it will streamline the entire process and save on time while still challenging the actual characters as they will need the necessary modifiers to beat the DC. Feel free to add in-game hints or unique items the characters can utilize that will give them bonus to the roll.

    Let’s now address my final complaint about this whole subject. This is completely my opinion and if you agree or even disagree, I would love to hear about it and why. Riddles should NOT be a required challenge. The reason it fits in movies and books is because the challenge can just be written in as being solved. There isn’t anything preventing a character from knowing the answer, while in a tabletop game, the limits of the characters are known and mechanically have a limit. This can lead to the above mentioned time waste. Getting the right answer shouldn’t be a requirement to move the story forward. Feel free to use it as a bonus challenge for more loot or to help with knowledge to make the next encounter easier. Just don’t make the story contingent on the solution being figured out.

    At the end of the day, each gaming group will have their own version of fun. Some may absolutely love the idea of trying to beat each other in riddle form and feel like it needs to be a requirement in a game. Others may love a hack and slash adventure. As long as you all are having fun with the game, then you are doing things correctly. Riddles seem to be one of the issues that to me is in need of a bit of refining. Hopefully, I have helped sparked some new ideas and helped your games go to the next level! Until next time, may the dice be ever in your favor.


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