I Love Losing in DnD

PLAYER RICH – WITH A FOAM SWORD IN HIS CHEST: Rich, my friend, my Dungeon Master, how could you let me and the party lose? You’ve betrayed us. We thought we could win at DnD and other tabletop role-playing games every time, but… (indistinct gargling noises as he falls to the floor)

Hey Game Masters, Dungeon Masters and players who’ve been sent to read this blog post passive-aggressively, let’s talk about losing.

If you think about the wide spectrum of things that we call games, then losing is a tricky word. It’s something we are trained from the beginning of our lives not to like, to avoid, to stay away from. Winning is everything.

Tabletop role-playing games still have at their roots that essence that losing is somehow a bad thing. If you trace the origins of the hobby back to the original Dungeons and Dragons games like Chainmail, their immediate ancestors were medieval battle war games, pitting one player against the other in a very adversarial position where every single time there would be a winner and a loser.

Now the TTRPGs that we play today, especially with my preferred variety of story and narrative first games, still share that bit of DNA with their ancestors. As players, often we’ll see the Game Master as this adversary, as an opponent.

What we’re looking at today is to begin a change of mindset – to sow the seeds, to help people realise that losing can be a ton of fun as well.

This blog post’s controversial opinion: I think most TTRPGs are too lethal.

I think that character death in many games is actually too frequent and should be used much more sparingly. However, I think that defeat for the party is not used nearly often enough. Rather than thinking that it’s winning or losing, it’s understanding that whatever the outcome of a combat or conflict, losing advances the story.

The story of something going right all the time from start to finish is boring.

We played a football match. We won – Okay.
But the game where you win – and someone scores a goal in the last minute to save the day, that’s got ups and downs and peaks and troughs, and chances that’ll be a much more fun story.

Applying that to our game tables, whether that’s in fantasy, sci-fi, modern day, any other genre you can think of, having this story with ups as well as big downs is what makes it more memorable, and for me at least I’d have a much more fun time with that.

But how do we apply it? How do we actually make that happen without railroading and forcing defeat on our players? Before we get to total party kills and those huge dramatic moments, let’s talk about smaller losses. As Game Master, you’re already doing this, these little small losses, every time you say the word “but”.

“You win the fight but one of them escapes.”
“You defeat the boss but the princess is in another castle.”

To give these narrative twists a bit of mechanical heft, there’s quite a few different things that we can do: Clocks, countdowns, timers are all so so good for helping your players realise that they’ve got to keep on pushing, they’ve got to progress.

Victory isn’t just defeating all of the enemies in however long they feel like. Whether you use a spin down dice to show turn trackers, or one of those not very tasty looking pies, or even a real time clock, each of these is adding not a victory condition, but a new loss condition. The party have to do the thing, but they also have to do it within this time, otherwise something bad happens, they do not get exactly what they want.

Once players realise that the total party kill isn’t the only way to lose a fight, they’ll up their game as well, they’ll do different strategies and tactics in order to defeat the Game Master.

But by normalising these different types of defeat, these different ways of not quite getting what you want, when it comes to something bigger, your players will already be primed. If as groups we close ourselves off from negative outcomes from the bad thing happening, we’re closing ourselves off from a huge range of human experience.

In the style of narrative first roleplay heavy games that I enjoy so much, I want to experience as much as possible of the life of the inner workings of my player character. How do they handle a setback? How do they bounce back? How do they react to a loss of a friend? It’s not the very very best day of our lives that defines us, it’s the worst day, and how we continue on, how we rebuild after that.

[[Mothership]] talks about playing as the characters on the very worst day of their lives. I love that so much. This isn’t your average Tuesday flying through space. This is something horrible, this is something so out of the ordinary, and seeing how your character, usually a normal person, reacts to the situation is where so so much lovely story gold comes from.

Again, it’s the highs feeling higher when the lows are lower. That contrast drives story.

An interesting philosophical question. What makes a good defeat?

For me, that good defeat is something where the story doesn’t just end, we don’t just pack up our toys and go home, but the story develops in an interesting way.

The very best defeats are the ones where winning is entirely possible right up to the last minute. And if they do lose, the players should feel like they were unlucky, or just made a bad plan, rather than feeling that they did everything right, and still got wiped out. Winning a high stakes fight should feel like a masterful skill. Losing should feel like bad luck, and the dice just were not in their favour that day. A fight that the game master sets up the characters to lose, and there is no way out, is not fun, even if you as game master are thinking “ooh, this’ll be cool, it’ll advance the story even further”. That’s railroading right there, you’ve decided what should happen, rather than giving possibilities.

One thing I love about playing so many systems, rather than just focusing on one, is that I can steal mechanics from anywhere, and patch them on to whatever I’m playing. The best known systems with interesting failure mechanics are games like Blades in the Dark, that come from the Powered by the Apocalypse family. It’s failing forward.

One that I’ve particularly been enjoying recently comes from the games The Between and Brindlewood Bay. In those games, if you’re doing something risky, the Game Master will ask you what you fear will happen if something goes wrong, and then they’ll say “no, it’s worse than that. If you fail this, this even worse thing will happen”. Depending on what feels realistic or right for the moment, there’s so many ways that this could be taken, but often the worst case scenario will be character death, maybe not even of the person rolling the dice.

The nice thing about both of these systems is that they have player meta-currencies, which can be spent to turn a failure into a weak success. So you still don’t get everything you want, but you’ve averted that nasty, nasty thing. But in these games, which are both very narrative and story-driven, those defeats, those bad moments, are exciting, and you find yourself wanting the bad thing to happen, just to see how your character will react.

Ironsworn and Starforged have similar mechanics, games where failure is much more interesting than success. Daggerheart is another game, while not powered by the apocalypse style, still uses this fail-forward mechanic to make things really interesting. I like that in Daggerheart, player agency and spending of meta-currencies even includes in death, if you’re down on zero hit points, that you can choose to go out in a blaze of glory, automatically succeeding at something. Or you can roll the dice once more, let life or death depend entirely on your hope and fear die.

I think that maintaining player agency in defeat is the secret sauce that binds all of these things together. In Brindlewood Bay and The Between, you can back down completely, you can hear the stakes, and then say “Nope, don’t fancy that, I’m going to do something else.” That open decision that keeps the story in the player’s hands, and means that players are going to be much more willing to take those risks, and if things fail, they still get to see where the story goes.