Riddling Contest Rules

Recently in game we had a friendly contest of riddles. Mechanically, here's how we did it:

Dungeons and Dragons 5e Riddling Contest Rules

1. There will be two rounds of riddles so each person will provide two riddles to be solved. Play in character but you can draw upon your riddle knowledge as a real person.

2. The winner shall be determined by points
1. 1 point for solving a riddle
2. 2 points for stumping everyone with a riddle

3. When it’s your turn to provide a riddle, you have two options:
1. If you, as a player, know a riddle you can provide it freely (we’ll assume your character would know some riddles)

OR

2. You make an Intelligence Saving Throw to draw a riddle or riddles from the bag. Once you draw a riddle or riddles, you must use it (or one of them if you drew several). Based on your saving throw result, you
1. 5 or less – Draw two riddles, read them, and provide the easier riddle to the group. Remove the second riddle from the game.
2. 6-10 – Draw one riddle and use it
3. 11-15 – Draw two riddles, read both, choose one and use it, remove the other riddle from the game
4. 16-20 – Draw two riddles, read both, choose one and use it, and return the other riddle to the bag
5. 21+ - Draw three riddles,  read all three, choose one and use it, and return the other two to the bag

4. Likewise, when it’s your turn to answer a riddle, you have two options. A person can only provide one answer to a riddle – the first answer counts as their final answer. The riddle ends when the correct answer is given.
1. If you, as a player, know or think you know the answer, you can yell it out. Anyone yelling an answer should go first.
2. You can make an Investigation roll. Based on the success of the roll, you (and only you) are provided with clues to the answer. Clues are provided first to those that roll highest.
1. 15 or less – no clues provided
2. 16-20 – A clue to the nature of the riddle is provided (perhaps it’s a language based riddle or the answer is an abstract concept)
3. 21+ - A clue to the nature of the riddle is provided as well as a clue to the actual word itself in the answer (for example, “It has four letters and ends with ‘t’.”)