Riddles for GMs Who Don’t Like Riddles

Let me make one thing perfectly clear. If you love puzzles that the players solve in Dungeons and Dragons, I’m not telling you that you are wrong. All I am going to say here is that I’m not particularly a fan of trying to have players figure out clever puzzles or riddles. If I don’t expect the PCs to provide proper descriptions for combat actions, I guess I’m not big on expecting PCs to explain crazy puzzles or riddles.

But wait, how can I justify this?

In one of the most iconic riddle contest in fantasy, Bilbo wins by coming up with a bullshit answer.

Riddler cheats all of the time–the crux of Batman defeating Riddler isn’t really solving his riddles, it’s following the riddles to places Riddler has been, so that he can then find clues Riddler didn’t intend to leave behind.

In other words, the best trick a riddle or puzzle can pull off is to make you think that the riddle or the puzzle is the important thing.

Despite this, answering riddles and solving puzzles is a trope in fantasy and pulp adventure, and it’s not something you want to leave out of your D&D adventures, even if you don’t want to read up on logic puzzles to throw at your players and then pretend that their characters figured it out.

Here is a process I’ve been toying with for adding in some riddles that don’t require the player to know the answer, but aren’t just a matter of a PC making a single ability check, either.

First Things First

Is our riddle or puzzle active or passive?

Active or Passive (i.e. someone asking a riddle versus a riddle presented in a book or on the wall of a tomb).


The character asking the riddle picks a skill. This determines the favored ability score and favored skill. The character then rolls that check to set the difficulty of the riddle.

The player character can make a wisdom (insight) check against the character asking the riddle, who opposes with a charisma (deception) check. If this is successful, the character knows the favored ability score and favored skill used for the riddle.

  • If the person asking the riddle allows the characters to confer, they gain advantage
  • If the player character guesses the right favored ability score and favored skill, they roll with advantage
  • If the character chooses the wrong favored ability score, they roll with disadvantage


The puzzle or riddle has a set DC, with a favored ability score and a favored skill. Characters cannot roll to “read” the puzzle as a passively presented puzzle will have no particular “tells.”

Most passive puzzles or riddles won’t have a means of preventing characters from conferring, but when magic gets involved, who knows? If the DM deems it makes sense, the PC solving the puzzle or riddle gets advantage from conferring with others

  • If the player character guesses the right favored ability score and favored skill, they roll with advantage
  • If the character chooses the wrong favored ability score, they roll with disadvantage
  • If the passively presented item is a puzzle, it may still require the characters to perform an action, which may still require other checks (for example, a dexterity check to set items in a certain pattern under a certain time limit, or a strength check to move a heavy item from one area of the room to another)

Wisdom Riddles or Puzzles

Wisdom riddles or puzzles are usually questions that have numerous solutions, where a character has to understand the context of what is being said to understand which of the fairly obvious answers applies in the current situation.

Intelligence Riddles or Puzzles

These are usually very precise riddles that lay out a complex series of variables that need to be evaluated to come to a single conclusion.


Combat is boring if all you ever mention are the numbers. Puzzles and riddles using this system fall into this same pattern. Based on the favored ability score and skill, make sure to add some details to what the actual riddle was. It doesn’t have to be complete, but it could be something simple like:

  • The favored ability score and skill are intelligence (history)–the puzzle could be a map with several famous names and locations on it, requiring the PC to trace the path of a famous general through their campaigns
  • In another instance, the favored ability score and skill might be wisdom (insight)–the puzzle is a map with three paths traced on it, and to solve it, the PC in question may have to remember a nursery rhyme about how important it is to look for the easiest path to follow, even if it’s longer
  • A riddle might have wisdom (medicine) as its favored ability score and skill, and it might be a play on words describing a disease and what organs are most affected by that malady
  • In some cases, this may even give you the opportunity to convey some information about the campaign world to the PCs that you wish them to know, while providing context that avoids an info-dump. They knew about that general, nursery rhyme, or disease all long, and you can convey the specific to them after they make the check to tell them what their character already knew


You can always switch things up by giving more player facing clues, like that there are tapestries depicting heroes of old in antiquated armor and clothing to hint at history being important, or explaining that there is soil and gardening implements near a puzzle that requires intelligence (nature) to solve.

As always, if you give this system a whirl, please feel free to let me know how it works out. I’ve used it a few limited times in my games, but I’d love to get a little more data on how it works long term.

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