Saturday, August 8, 2020

Improvising Riddles

It was requested that I write more about prospecting in Hell, so instead here's how to improvise riddles.

Lo, your party has been defeated by a foe, or else needs to pass by a bridge, or else needs to please a cruel queen, and they mercifully allow you to have your will, but only if you answer a riddle. Your GM, naturally, has not prepared this encounter and already used up their back-up riddles. What do they do?

1.Riddles of Assumption

They tell you a tale of a strange happening, where people respond strangely to what they see, then ask you why they respond in that way. The trick is that they failed to tell you something that you would assume.

Example: Roscoe and Willy are born on the same day, but Willy will die long before Roscoe and it won't be a great loss. Why not? Answer: because Willy is a dog and Roscoe is an elf.

2. Items Oddly Described

They describe something, usually a mundane object or a shadow, as though it were something else, like a beast, then asks you to tell what it is. Alternatively, the riddle is given in a dungeon and interacting with the object in question reveals treasure or a hidden door.

Example: I am a bag that's constantly blowing about with a wind. I am old, but never need to be repaired. The meanest beggar has one, but ancient kings have lost theirs. What am I? Answer: I am the lungs. (Ignore this paranthetical. It's just here to make the spoilertext longer.)

3. Puns

A hybrid of the previous two. It seeks the unity of two different things called by the same name. Usually this riddle type is kind of idiotic.

Example: I am a prodigal, yet indispensable for making heaps. What am I?. Answer: a rake. Ha ha.

4. Demonstrations of Wisdom

Open-ended riddles that are essentially challenging the victim to come up with an impressive answer. Usually cruel to spring on players unless they know they're dealing with an open-ended riddle, and that saying "there is no answer, you bully" will get them nowhere.

Example: What have I got in my pocket? Answer: the answer to this riddle.

General Guidelines

  • Remind players they don't need to answer the riddle. They can try to fight, run, or return to it later.
  • Try to ask a question at the end of the riddle so they know what they're expected to come up with.
  • Remember this riddle comes from the villain's mind. The answer should be something they know about.
  • If they only get one try, make sure that their answer is their final answer.
  • If they want to quibble with the riddle-asker, let them. I usually assume whoever gave them the riddle dislikes alternate answers (except for demonstrations of wisdom,) but that any audience will be sympathetic to good answers and will heckle perceived unfairness.


  1. A nifty quartet right here. What about the classic "mistaken maths" ones? Like, "if there are seven brothers in a family and each of them has a sister, how many children are there in the family altogether?"

    I guess that would be an assumption one as well, but rather than it being an assumption that the riddler doesn't tell you, it's an assumption that the players are more likely to have.

    1. Those are clever, and have a good variety in application.