It has been a solid 32 years today since I made my first full-blown regrettable choice. I like to keep track of these things, but I’m not terribly good at tracking my progress in the wake of a self-imposed train wreck. But 32 years on down the road I’d say I am making some progress towards improvement. Had the fellow on the news not said “today is October 3rd” it likely would have rolled right on by without being noted.

Dungeons & Dragons is kind of a celebration of regrettable choices. There aren’t many venues in which slip-ups and mistakes actually make things more fun. These are the kinds of things you actively try to avoid. D&D however is the exact opposite. One of the players in the game I run recently said “this might be a terrible idea, but it will make for a better story” before declaring their character’s actions. It was a terrific idea, and it made for a fantastic story. If you aren’t screwing up then you probably aren’t having as much fun as the rest of us.

Here are a list of some of my favorite regrettable choices from Dungeons & Dragons. A lot of good times and laughter in these booboos:

1. Character declared that they climb the wall and lay down on the top of the wall before asking timidly if there are spikes there.
2.  Character hears something rummaging in the bushes, so they reach in and pull back their hand with a badger fully engaged in wrecking their arm.
3.  One character heads down a spiral staircase, and the next character decides to sit on their shield to just slide super fast down the stairs, whereupon they slam smack into the first character and kill them.
4.  Character has a magical spear for slaying dragons, and a shield to protect against dragon breath attacks, but decides to sell both of them before going to fight a dragon.
5.  Characters decide to try and charm a dragon and one of them rolls a critical fail which gets everyone engulfed in a cloud of chlorine gas.
6.  Character decides to spice up the game by shooting a random NPC who then promptly dies.
7.  Characters discover a slayer genie and decide to send it after one of their fellow adventurers, but screw up the name so badly that it goes after somebody else entirely and ends up murdering an important NPC ally.
8.  Character is turned pink due to a failed attempt at spellcasting.
9.  Character catches an enemy and ties them up. Threatening them with a sword, they demand a yes or no answer to the question “why were you following this ship?”
10.  Characters ask an NPC for help without knowing anything about the NPC and how they function. Help was provided, but a completely innocent fellow was bashed up in the process and now the characters are in hotter water than they were before.
11.  Character fashions a crude hang glider from a dead dragon’s wings and uses it to dive down a mountainside to slam right into the chest of a fire giant. Fire giant dies from falling off the rest of the mountain, the hang glider is ruined, and the character manages to somehow roll out of the wreckage with a handful of hitpoints left.
12.  Characters head out on a secret mission and almost arrive at their destination before realizing they had forgotten their disguises.

Have a terrific Regrettable Choices Day, everyone!