Natural 1

Finding Fun While "Losing"

I love to fail when I’m playing D&D! Seriously. Coming up short is arguably my favorite thing in the game. It’s not a masochistic enjoyment of not being “good” at the game or knowing the rules. Losing is what gives a win any type of meaning. Trying to do something and falling just shy of the mark can be heartbreaking and rightfully so. But when you finally overcome that hardship or character defect the result is so much more fulfilling. Through failure we are enhancing the story we are telling at the table because a story without struggle is BORING!

Whether I am a player character or a DM getting low rolls often leads to very memorable moments, struggles, conflicts or improvised shortcomings I wouldn’t have come up with on my own.

Maybe the big bad guy that the party has been chasing for the last 4 sessions finally has them in his lair, he seems to have all of the cards, delivers a big dramatic monologue, we roll initiative and… boom nat one. This suddenly creates a massive juxtaposition from being a larger than life figure to getting hit by a group of people before he even gets to act. When this type of thing happens it breaks the tension of a moment and gives people at the table a momentary win which can give folks a nice laugh and false sense of security when the tables turn back against them, making the big bad a real threat again. That quick win provides a comedy beat before diving back into tension of intensity and renews the sense of urgency. The other golden opportunity as a DM in that moment is in how the villain responds sets the tone for rest of the encounter. If the tone at the table is meant to be dark and sinister you can have the BBEG say something to the effect of “You all aren’t even worth my best effort, my minions will make short work of you.” If the tone is more playful you can acknowledge the roll and have the big bad comically fumble “Oh no! I dropped my wand… hold on one second.”

These moments for a DM are great but often we stack odds in favor of our players to make victories difficult to come by so that they feel earned, but still happen more often than not. It can be a tough balance to find at first but something I found helps me is looking at each session as a chapter in a book or an episode of a TV show. Each location is treated like arc of the story or TV season. You have some plot hooks ready to start the arc, your players inevitably do something unhinged that you didn’t plan for which leads into rising action; then they face some type of adversity whether it is through losing a battle or a set back in an investigation and finally culminating in a positive or negative resolution from the initial hook. This loose structure in focused settings slowly builds wins that feel satisfying even when they are very small. The things that tend to stick in people’s memory is more often a moment in overcoming a failure rather than a killing blow.

From the PC perspective, rolling a failed skill check, losing a battle, or having an encounter go horribly wrong is such a wonderful chance to enrich your story. These opportunities are the perfect chance at keeping the story we are all telling together grounded in humanity. Are the characters we play exaggerated and larger than life? Sure but a character that is one-note is ultimately very boring to play and play with (at least in my experience).

Let’s say for example: You are playing as a dwarven monk who is from a hamlet and you were the most gifted athlete in the small village and you have rarely (if ever) faced a really tough challenge. You’ve met some other adventurers along your journey so far and the first group of other adventurers you run into is a bit boastful. Being the prideful dwarf you are, it’s your chance to show off your skill and challenge their best to spar. Even if you are better tactically and mechanically the dice rolls are not going your way. Their dwarf fighter just keeps getting over on you.

Instead of looking at this as bad luck or losing, it is really a great opportunity to start looking at your character as having some shortcomings that they can start to learn and grow from. You get to decide how your character reacts to this and learn and develop a deeper story. Are they quick to anger and resentment? Do they become depressed? Are they more inclined to shy away from certain types of people or creatures? Do they learn from their mistakes quickly or do they tend to dwell on them? Do they now look at the person who bested them as an equal, a rival, or someone to avoid out of shame?

These are all great additions to one of the several stories that are being told through the lens of this fantastic game that we play. I encourage players to think about some of these types of things when we are going through character creation but I also remind them to leave some things unanswered to begin with. You can find a lot of missing pieces of a character through time at the table and in these types of moments where nothing is going according to plan. When the chips are down true character tends to reveal itself.

An important thing to take away from this as a DM/GM is making sure to give your players the opportunity to fail and succeed in nearly equal parts. The balance that you find at your table is going to look different than mine or anyone else’s. Embracing struggle and difficulty is what creates tension and helps characters grow. Stories are the most compelling and satisfying when there is a legitimate threat of failure in whatever form fits best for the collective story. For myself and my table, winning isn’t about who did the most damage, found the most gold, or if the party finally got the MacGuffin to defeat the evil lich. What I consider a real win is finding a way to tell a satisfying, grounded, human story that everyone at the table enjoyed.

Kyle