TLDR: Riddle puzzles in DnD can suck, but I’m going to show you how to make them work by shifting them from hard-locking progression to soft-locking optional content.
Video Version of this post: https://youtu.be/X2CFVkxyFfg
Puzzles, riddles, prophecies and mystery are all ideas core to the adventure fantasy and thus many a nascent dungeon master's first instincts lead them to put a riddle wall in the middle of their carefully constructed dungeon. When the adventurers approach it, the Dungeon Master expertly orates the verse strung from their mind or stolen from books, movies, or Riddles.com.
Then, their words hanging in the air, the dungeon master leans back, ready to sit smugly by while their players puzzle and agonize over the answer.
“Um, what was...can you say it again?”
The Dungeon master repeats the riddle, more clearly this time, emphasizing key words as clues.
“Uh, yeah, um...can you just write it down?”
The Dungeon Master furiously scribbles the riddle onto a piece of paper and forks it over as the players collective headache fills the room.
“Is it a cow?”
“I think it’s the sky.”
“Can I just make an intelligence check?”
The Dungeon Master’s smile fades. That’s no fun. You might as well have said “there is a riddle on the wall, make an intelligence check to see if you can figure it out.” Wait, why didn’t you? The player’s intelligence isn’t necessarily reflective of their character’s intelligence, right?
Well, except that the player makes stupid decisions in combat that their character might not make, so why is this any different? Wasn’t this supposed to be fun and cool? Why does this suck? Why have we been in this same room for half an hour and now nothing has happened?
JRR Tolkein is famous for his command of language, thus song, verse, and riddle feature prominently in all of his works in Middle Earth.
Let’s think about what happened in the Lord of the Rings if JRR Tolkein was running an adventuring party when approaching the Mines of Moria.
Tolkein: You skirt the edges of a stagnant lake of black, brackish water at the base of the mountains and approach a wall of smooth rock. Gandalf, your foreknowledge of dwarven architecture allows you to find the Door of Durin just as the moon strikes the stone and lights up the runes etched upon it. Does anyone speak Elvish?
Legolas: I speak elv-
Gandalf: Yes of course, as a great wizard of legend, I speak elvish.
Tolkein: Alright, translated to common, the runes say: Speak friend and Enter.
Gandalf: Um...I cast the “Knock” spell on it to open it with my great and powerful magic.
Tolkein: Nothing happens.
Gandalf: ...I try again.
Tolkein: Nothing happens.
Gandalf: ……..any ideas?
Gandalf: Okay, let’s make camp.
Tolkein: You’re not even going to try to figure it out?
Gandalf: I just cast two knock spells, I need to rest to try again.
Tolkein: It didn’t work the first time, so why do you think - sigh
fine. You make camp. As time passes, one of the halfling NPCs disturbs the water because he’s bored. The stagnant water starts to move.
Gandalf: That little shit. He’s going to get me killed.
Tolkein: So are you doing anything?
Gandalf: Have I got my spell slots back?
Gandalf: Then no.
Tolkein: FINE. The other halfling NPC approaches as says, “Speak friend and enter...hmm...Gandalf what’s the Elvish word for friend?”
Gandalf: Well, my dear boy, of course it is (hey, DM, what is it?)
Gandalf: Melon? Didn’t you spend like years on this language? Why is one of the words just “melon.”
Tolkein: The water gets more turbulent.
Gandalf: It’s Melon!
Tolkein: The door opens. Finally. As you all go inside, a monstrous creature bursts from the water and -
Gandalf: I close the door.
Tolkein: crumples up paper
Okay, well I guess that encounter isn’t happening.
You might have noticed the problem in running this encounter for the DM. They attached their riddle to the only door moving forward, effectively hard-locking their players out of further progressing the story until they’d worked it out. This sets you up for two situations: Either they figure it out and move on...or they’re stuck.
The characters in Lord of the Rings had to camp outside the door for hours while Gandalf tried and failed to outthink the Dwarves, when the answer was as simple as can be.
This is the experience you are accidentally trying to emulate when including riddles in your game. So does that mean you should just take them out?
Well, that’s a simple solution, and one I’d recommend if the other option is doing what just happened in Lord of the Rings. But, if you love the idea behind a good riddle, I’m going to help you out.
90% of the problems you’ll encounter when including riddles in your gameplay is placement. If you put a riddle on the only door forward, that nearly guarantees that your game is going to come to a screeching halt.
What if you give that riddle to a monster? That way the party can either answer the riddle or get into a fight. For instance, what if the watcher in the water rose from the lake and gave them a cheeky riddle?
This is better than the riddle-on-a-door puzzle, but not by much. When I’ve seen this employed, players still agonize forever about the riddle before getting into a dangerous fight with a gatekeeper monster because they rightly assume that it’s going to be too strong for them.
I’m going to tell you another way to do it: instead of using a riddle to guard the way forward, use a riddle to lock secrets away. Let me tell you what I mean.
In Matthew Colville’s Delian Tomb, he sets up a dungeon with a history of an order of knights devoted to fighting chaos. You find an inscription in the first room with their creed: “I swear to fight chaos in all of its forms, to uphold order, by honor of my word.”
This is important. It’s a primer to the world of the dungeon, but also serves as a hint, foreshadowing the riddle to come. After beating the boss in the main room, the party can find a statue with an inscription that reads: “If you are to keep this, you must first give it to me.” If the party answers “my word” or any variation of that, a secret door slides open, revealing a hidden tomb with some angry skeletons and a treasure inside.
The players don’t need to do that, though. They could just as easily kill the boss, save the princess, and bounce because they did what they came there to do. But that’s not what DnD is, right? The quest is just the hook. When you get into the dungeon, that’s when things get interesting.
The beauty of this design is that it perfectly accounts for every kind of player. The deeper lore rewards attentive and clever players without punishing those players who just want to kill things and check off boxes. It’s elegant, as deep as you want it to be, and most importantly doesn’t kill the momentum of your game.
One last piece of advice is not to be super adamant about the correct answer to a riddle. If the players come up with a good idea that adequately captures the spirit of the riddle, feel free to say that was the answer all along. Use your own discretion on this, you can play it as hardball as you want for the situation.