What rhymes with riddle? Part 2

Aron Christensen
Published in
4 min readApr 12


A shadow swoops over the road, momentarily blotting out the sun. The dragon whose hoard the party so recently raided has tracked them down at last. It opens its mouth, destructive force gathering deep in its throat to pour out in a stream of pure revenge and… You jump up on the table and kick the players in the face! Wait, no, that’s not how we do combat. The players sit comfortably, eating Cheetos and showing off their pretty custom dice. When we roll initiative, their characters must battle the dragon.

When our games include other kinds of challenges — talking their way past the guards, playing a song, and solving a riddle — I often see the Storyteller expect the players to perform the task. Most likely, not everyone at your table has been in a band, been in the debate club, or is any good at riddles. But bards, military officers, and sentient computers should be good at those things. When faced with a riddle or puzzle, don’t be afraid to let the characters solve them.

Image: A green chalkboard (remember those?) covered in a variety of algebra and geometry problems. And some smiley faces.

Roll for it

Just before the pandemic, I was Storytelling with some new players. Not just new to my table, but entirely new to role-playing. Erica and I are used to high RP play, but our new players weren’t even comfortable speaking in character yet. That’s okay. Role-playing is a form of public speaking, just to a very small audience. (Unless you stream your games online.) It’s acting and it’s improv, and not everyone is good at it. At the very least, no one starts out good at it. So I tried to make it safe for them to say I talk my way past the guard. My new players made a roll, and because their character was good at lying, they succeeded and then we went with the result.

Riddles and puzzles are a vital place to remember that. Not everyone is good at escape rooms, not everyone has read a riddle book, or is even good at rhyming. (Even on Critical Role, some of the cast visibly struggled to rhyme their way past a guardian… and they’re professionals!) But a player who has rolled up a wise druid, a brilliant wizard, a living computer, or a psychic alien is a different story entirely. Those kinds of characters should be good at solving puzzles and riddles even if the player isn’t. So should the wizard come off as an idiot because the player doesn’t do well under pressure? Of course not! A player that chose to play a genius wants to feel like a genius. Let them roll those big-brained stats and excel where their character should excel.

Riddle with yourself

Consider coming up with some riddles and rhymes of your own. Keep them behind the screen and when a character chooses to use History to deliver a riddle, pull out your history-based question. An NPC can tell it. “Oh? The third king’s son, the third day’s sun, the third battle won? Good riddle, yes, a very good riddle. But the answer is [insert something clever]!” It’s a way to bring a bit of that role-play back into the challenge without making the players come up with that stuff on the fly. It’s easier for the Storyteller to do some prep ahead of time and then hand out riddles to the characters that succeed on their rolls.

When players actually answer

Not every player is a genius at riddles and puzzles, but some of them are. Some players love riddles or read a lot and have exposure to riddles. So sometimes you may present a riddle or puzzle — or a note-quite-a-riddle like we talked about back in part 1 — and BAM! Your player spits out the answer.

Even if it’s not really feasible for their character to know the answer, the player shouldn’t be punished or ignored for success. Actually, they should likely be rewarded for being good at something. But keep the rewards small — a player that’s been in a band has an unfair advantage during a musical challenge.

Riddles and puzzles are a fun part of role-playing games and make a nice change of pace from combat scenes or heavy RP. Just remember that there’s a difference between players and their characters — we can’t expect our players to be able to do everything their characters can. After all, during fight scenes we don’t expect players to actually fight and be good at it. Leave that to their characters.