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Failure is Fun in 5E D&D

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Failure is fun. You read right — one of my favorite things in fifth edition Dungeons & Dragons is failure. What’s more critical failure is one of my favorite optional rules to use in any 5E D&D game. Pulling from the Nerdarchy vault today I discovered a video from our archives that exemplify much of what I’m saying. Let’s talk about why.

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Forward failure in 5E D&D

One of my favorite concepts from a non-D&D RPG comes from Open Legend with the idea of failing forward. This means when characters fail the story progresses. Part of why missing an attack roll is boring is because it stops your turn there. No more dice rolling or interesting narrative unless you critically fail, in which case you get to work with the Dungeon Master toward a terrible consequence.

Ultimately this is what I like most about critical failures and why failing in general is so interesting in 5E D&D. When you fail there are consequences. If you fail in a video game you simply try again until you succeed and while that’s all well and good it feels like a delay or possibly even a waste of time.

When you fail forward there’s a consequence for failure. This consequence might present a new complication or it might result in a different type of success being achieved to overcome the scenario. Narrative consequences distinguish 5E D&D from video games and make for more engagement when such things occur. I absolutely love when characters fail because it opens doors for further narrative and builds suspense in the game.

“Rolling a 20 or a 1 on an ability check or a saving throw doesn’t normally have any special effect. However, you can choose to take such an exceptional roll into account when adjudicating the outcome. It’s up to you to determine how this manifests in the game. An easy approach is to increase the impact of the success or failure. For example, rolling a 1 on a failed attempt to pick a lock might break the thieves’ tools being used, and rolling a 20 on a successful Intelligence (Investigation) check might reveal an extra clue.”

— Critical Success or Failure from the 5E D&D Dungeon Master’s Guide chapter 8: Running the Game

Combating failure together

A really big reason I like failure so much is it opens the pathway for other players to engage with an event. If my character fails at something another character can intervene and try to influence the scenario. Not only does this build camaraderie in a game and at the table but it allows others’ characters to shine in their own rights and lets fellow players develop their characters through action instead of words alone.

There’s nothing quite as satisfying as overcoming a difficult challenge together as a table. When more people get to participate it makes everyone feel more special and engaged and leads to better immersion and deeper investment in the whole session.

How, why, and what of failure

When failing I find you should never simply accept a failure as-is. Instead ask yourself how the failure occurred, why the failure occurred and what needs to happen to resolve the complications of the failure.

One thing I love as a player is when a DM lets me lend to the descriptions of how my character fails. It’s one thing to fail and have an interesting outcome but it’s wholly more satisfying when the DM lets me describe how my character fails. Usually when this happens the DM will interpose some of their own interpretation of my character’s actions, further developing the consequences of the failure and offering a few evocative descriptions to paint the picture more vividly for everyone at the table.

Failure is one of the most interesting ways to develop a character. Not only is it telling as to how a character responds to a failure but even the act of failing itself can really lend to character flavor. Ask yourself why your character failed.

Maybe your Shadow Magic sorcerer didn’t just drop the bowl that shattered. It passed directly through her hands unexpectedly. Perhaps your barbarian failed his persuasion check not because he was unconvincing but because of the ale smelling belch that erupted unexpectedly in the middle of what he was saying.

Think about how your character’s personality, abilities and traits contribute to failure. Overthinking an attack is a viable reason to miss. Struggling with persuasion is more interesting when the failure is a result of your character’s reputation for being so good at deception.

Once you know how they failed and why you can ask what your character and their party can do to overcome the consequences of the failure. As already mentioned, combating failure together builds a sense of togetherness. Part of what makes diverse parties so interesting is they make up for one another’s weaknesses. This even mirrors true life.

Knowing what must happen to respond to failure keeps the story moving and prevents the narrative from grinding to an untimely halt.

Matters of life and death

Real talk — sometimes failing sucks. When this happens it doesn’t have to mean 5E D&D stops being fun though. Let me explain.

Failing is to success what death is to life. What I mean is the distinct and very real possibility of failure is a big factor of why success is so special in 5E D&D. If everything is handed to my character on a silver platter I’m usually bored pretty quickly.

This is a big reason I like having a couple of utterly abysmal ability scores. Not only does this let me describe the eccentricities of why my character has a 4 Charisma but it makes when I succeed on a Charisma check much more satisfying. I love the moment when the least likely person to say the right thing says exactly the right thing for the situation.

The rest of this section contains spoilers for Critical Role Campaign 2. Ye be warned.

One of my favorite moments in Critical Role was when Molly died. Reinforcing the mortality of the game in such a way prior to anyone having any form of resurrection really made the possibility of death sink in. It made every combat thereafter so much more intense, not to mention cementing that villain as a true threat.

The tragedy was compiled by the fact the Mighty Nein were trying to rescue Fjord, Jester and Yasha who had been captured by this villain. I remember watching the moment with tears in my eyes and realizing for the first time the prisoners were in very real danger.

That moment of failure made the entire campaign so much more powerful, set events into motion for much later into the story and made the whole thing feel even more worth it. The failure is something that will forever remain one of the most emotional moments I’ve had watching anything on TV, experiencing any story.

Final thoughts

Failure holds so much more potential than a simple “miss and move on” moment whether exploring why the failure happened, how the failure happened or what to do in response.

Hopefully I’ve convinced you to consider failure and its many possibilities — for storytelling, for fun and for friends. If you’ve gotten something out of this article please leave a comment, tweet us @Nerdarchy or connect with us on our Facebook page!

*Featured image — The oceans demand a price be paid in Fish Food, one of 55 dynamic encounters ready to drop into your game in Out of the Box. [Illustration by Kim Van Deun]

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Steven Partridge

Steven Partridge is a published fantasy author and staff writer for Nerdarchy. He also shows up Tuesdays at 8:00pm (EST) to play with the Nerdarchy Crew, over on the Nerdarchy Live YouTube channel. Steven enjoys all things fantasy, and storytelling is his passion. Whether through novels, TTRPGs, or otherwise, he loves telling compelling tales within various speculative fiction genres. When he's not writing or working on videos for his YouTube channel, Steven can be found lap swimming or playing TTRPGs with his friends. He works in the mental health field and enjoys sharing conversations about diversity, especially as it relates to his own place within the Queer community.

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