You guys ever play Monkey Island? What about Sam and Max? Day of the Tentacle? Grim Fandango? All of those point and click adventure games share a similar structure of barrier, investigation, frustration, and eventual progress.  You’ve got to figure out what the game designers were thinking in order to beat the game, and that can be a little like peering inside a madman’s skull. There was one puzzle in Curse of Monkey Island that I remember struggling with for hours. Apparently you’re supposed to spot some dandruff on a coat, which turns out to be lice, which needs to be planted on a comb, which causes the weirdly Scottish hairdresser over at the Barbery Coast to take off a well-coiffed antagonist’s hair. This was by no means intuitive. I got stuck on the “frustration” part of the experience, and I wound up resorting to my very first video game walkthrough in order to make a little progress.

I bring up Monkey Island because, even with its bright animation and cheerful Caribbean soundtrack and amusing script, it still wound up being too much for me as a player. I damn near hurled the game disk across the room like a Frisbee. This is not the sort of emotion you want to introduce to your tabletop.

Riddles don’t change too much when they cross over from the computer screen to the gaming table. Players still have to guess what the riddler is thinking. But where a point and click adventure game is crafted to convert frustration into cathartic eureka moments, TRPG riddles are a little less reliable. Players don’t have the choice to give up and come back a few days later. It took everyone two weeks to schedule game night! That means you’re obliged to sit there, wandering what the hell the talking door or the animated painting or the floating head of Jambi the Genie wants you to say.

Now despite all of the above, I still happen to like player-challenging riddles in my games. The key is to make them optional. Answering the riddle will get you a nice bonus, but it should never be the only solution. This particular tactic came up in a deliciously meta moment in my megadungeon campaign last week. STAN! had put an imposing fire elemental in the party’s path, and it demanded that they answer THE RIDDLE OF FIRE to progress. This turned out to be nothing more than a game of 20 questions, and the elemental was freaking terrible at it. He bumbled his way through the game, forgetting to explain that only yes/no questions were allowed, giving contradictory answers, and generally frustrating the players by smacking them for fire damage whenever they guessed wrong. The answer is either A) you’re thinking of yourself you big flaming jerk, or B) I attack the fire elemental. My players went with the latter, and were supremely satisfied when the dude’s dying words were, “Best two out of three?”

So riddle me this: Have any of you guys used riddles in your games? Was it successful? Let’s hear your stories (and your riddles!) down in the comments.