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Riddle Me This: Turning Riddles Into Story Hooks In Your D&D Game

This is the truth of the Riddle, children… that we make of our lives what we will. Destiny, purpose, fate… all stories in the end. And your greatest desires? Yet one more story. Make of it what you will, mortal children, but make it a good one.

Leolemus, the Sphinx

Riddles. They are a part of some of the most legendary fantasy stories ever… the Sphinx of Ancient Greek mythology requiring travelers to answer a riddle correctly or being torn to shreds… Bilbo Baggins being able to keep the One Ring from Gollum… the riddles of Gunslingers like Roland Deschain.

Unfortunately, at the game table, there aren’t many things that will bring me out of character and break my immersion more than a riddle. While this is from my own experience of them, I have yet to find one that doesn’t rely heavily on Dave’s wit, logic, and ability to turn a phrase rather than the character I’m playing. I think back to some of my characters, like Roderick Draughall, my bard from our Storm King’s Thunder campaign, or Guiden Iskrage, my wizard in our Journey to Ragnarok campaign; both of whom are genius-level intellect, people who live in those worlds, and they are relying on me, DM Dave, to somehow answer this brain teaser.

But, as I said, there are few things that are so integral to fantasy stories than riddles, and if you ever want to have a Sphinx show up in your adventure – riddles are part and parcel. So, what to do?

In a recent session of the Dragonlance: Shadow of the Dragon Queen campaign that I’m running, I was inspired to introduce a Sphinx, named Leolemus, and have him ask the characters the required riddle – but, from wherever the idea blossomed from in my mind, this was not going to be the type of riddle where the players sit around and try to pierce my wordplay – this was going to be a riddle that built out there individual stories to allow the characters to answer the most important riddle of all: who they were.

The Set-Up

Anyone currently running Shadow of the Dragon Queen will quickly wonder how they missed the Sphinx in the story. Don’t worry – you didn’t.

In the Floating Citadel of Lord Soth, the characters discover that there is a magical artifact, the Mirror of Reflected Pasts, that can help them face such a formidable foe as Soth. Simply put, it’s a plot device so that you don’t drop a CR 19 baddie onto a party of 11th level characters – more on this in a future article.

But, the Mirror is located in a secret room found by solving a riddle and maneuvering a statue into position. Pretty classic D&D tropes, and absolutely nothing wrong with them. But I started to think about how this could be made more exciting.

It was here that I challenged myself to create a riddle that would require all the characters (not players) knowledge and stories, as well as serve to truly add to the story of these heroes, and not just be another riddle that you solve and move on.

The Riddle

5 Riddles Shall I Ask, 5 Answers Shall You Provide. But first I must ask… what is your heart’s greatest desire?

Leolemus, the Sphinx

This was the “riddle” that I placed before my players, a quick perspective change that placed the emphasis less on some arcane logic puzzle, and more onto the characters themselves. To prepare for the encounter, I texted the players individually to let me know what their characters greatest desire might be.

With this information in hand, I went about the creation of an entire encounter that would serve to turn the Sphinx’s Riddle into something quite memorable for the campaign, as well as serve for a late-game capstone on the character’s journey and story arc through the entirety of the campaign. As we have discussed before, I had leaned heavily on the Narrative Side Quest mechanic for the whole campaign, allowing an immense amount of character development, much more than a monthly play schedule would usually allow.

Leolemus’ Challenge

For the actual encounter itself, I decided to play on the 4e mechanic of Skill Challenges. The Skill Challenge is an easy way to turn an encounter into something more narrative and character-centric without slogging yourself down into the crunchiness, and possible slog, of a combat encounter.

With the knowledge of the characters greatest desire, I created individual set pieces that Leolemus would place the characters into. I will admit that I was inspired partly by the Test of High Sorcery that is part of the lore of Krynn and Dragonlance (even if we couldn’t use it in our campaign, as there were no wizards in the party!)

Each encounter was tailored for the individual characters but the rules of the Skill Challenge remained the same:

Leolemus’ Challenge – All DC 15

  1. A character cannot use any skill or ability more than twice.
  2. One check is performed at a time, going around the table.
  3. Four successes are required before three failures to succeed in each challenge.
  4. If any character fails a roll, another character can lend them aid, but they will then roll their next check at Disadvantage.

If the characters succeeded in their challege (which they did!), Leolemus gifted them the Mirror of Reflected Pasts (renamed the Mirror of Erised), and provided them a Heroes’ Feast.

If the characters failed, as required by the lore of the Sphinx, Leolemus would attack and it would become a combat encounter.

Final Thoughts

Anytime that you have the inspiration to do so, look at upcoming encounters and see if you can turn them back onto the players. In this case, a Sphix’s Riddle turned from something that would place more emphasis on the players than their characters and, if we’re being honest, would barely have even become a footnote in the campaign.

Instead, a riddle and puzzle in the actual adventure of Shadow of the Dragon Queen turned into an incredibly exciting, fun, and memorable moment for every single player in the game, including myself as the DM. Placing a capstone on the characters journeys, and allowing the space for them to create said capstone, right before what was going to be the Big Battle and finale of the campaign was perfect.

Until next time, Heroes… LIVE THE ADVENTURE!

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