Discourses on DND

November 7, 2025

22 min read

tl;dr

a lot of people have an idea of what dnd is lodged in their brain, both those who have and havent played it. i think the dominant mode of playing dnd is largely missing out on what makes it cool and unique from a traditional board games. you should only feel obligated to engage with dnd's rules and setting and player culture to the exact degree you must to give yourself license to let loose and play some make-believe. also i have some tips for how to make your dnd campaign better.

A Parable

As a tween, I stumbled upon an eccentric community of Lego wargamers called BrikWars.

I quickly became obsessed with the system they had developed. I printed out the rulebook pdf onto copy paper, 3 hole punched it, put it into a quarter inch binder, and started forcing any and all of my friends to play it with me. BrikWars was a revelation to me, because I had reached the age where make-believe was starting to be seen as cringe and childish. But video games and board games, constrained by some arbitrary set of rules, were still acceptable. BrikWars managed to successfully straddle that line by wearing its disdain for its own rules on its sleeve. If you will permit me a rather longwinded quotation from the rulebook:

1.3 Proper Observance of Rules

Rules are for the small-minded and weak. Let some first-graders loose with a collection of bricks and watch the way they play. All the drama, death, and explosions anyone could want, and they won't have to crack open a rulebook even once.

How is it that they're so much smarter than adults? The answer is that adults have been subjected to many more years of forced schooling than the kids have. Wait until the kids turn eighteen; they'll have become just as slack-jawed and dull-eyed as any other Human.

BrikWars has a lot of rules. Players who've felt the sting of the compulsory education system will respect these rules, because the rules are written down in a book and some of them are even capitalized.

For players whose lives went so badly that they attended college as well, there's a risk that they'll not only shackle themselves to these rules, but will then twist them to their own ends, weaseling out loopholes and exploits to cleverly frustrate the other players and ingeniously prevent fun for the entire group.

Players engaging in rules-lawyering and munchkinism have missed the point of BrikWars. If possible, they should schedule some time with actual children and try to remember all the things they've forgotten about having fun.

The reason BrikWars has so many rules is that it's a lot more fun to flout a large rules system than a small one. Rules should be treated as a springboard for imagination rather than as a leash for self-enslavement. But not everyone is ready to live without the safety net that a rules system provides, so before going any further, here are the three most important rules in the game:

1. THE RULE OF FUDGE
Fudge everything your opponents will let you get away with.

2. WHAT I SAY GOES
Players are smarter than rulebooks. Especially the ones with the highest dice rolls.

3. EVERYONE'S THE BOSS OF THEIR OWN TOYS
Don't break people's stuff without their blessing.

Reading this for the first time was a revelation to me. Brikwars knew exactly what it was: a justification for grown-ups to play with legos. Not collect them, not assemble and display them like Will Ferrell in The Lego Movie. To truly play make-believe, with characters and stories and violence and explosions. If someone wanted something else out of their wargame, well there was always Axis & Allies for the extremely patient or Warhammer 40k for the extremely wealthy or Commands & Colors for the extremely nerdy (I actually have a soft spot for this one, but I can never find anyone to play it with me). Each wargame pointedly fills its niche, and though Warhammer probably has the greatest mainstream mindshare among them, I think people tend to know what they’re getting into when they order $150 worth of unpainted plastic marines.

Get to work!

It would be a shame if one wargame called something like Dogfights & Divisions managed to corner all of the publicity and name-recognition, and anyone who thought “maybe I should try a wargame” landed on D&D as the only game they could assemble a group of normies to play. But then everyone who is convinced to play D&D comes to it actually wanting to play something more like A&A or C&C or BrikWars, but there’s never enough sustained collective interest to shift the group to one of those alternatives and so the entire play experience is quite unpleasant for most everyone involved and they swear off wargames forever.

You may be able to tell where I’m going with this. I think Dungeons and Dragons has successfully sucked up all the oxygen in the tabletop roleplaying game (TTRPG) space, which is both cool (as it’s an increasingly mainstream way for adults to allow themselves to play make-believe) and unfortunate (there are infinite ways to do a TTRPG but most people begin and end with DND). DND itself is painfully aware of the situation it’s in.

A Brief Introduction to DND

Skip to the next section if you already know how DND works.

Dungeons and Dragons is a game played primarily in the minds of its players, utilizing a light physical apparatus to assist in keeping track of details. It is typically set in a high fantasy world, reminiscent of something like Lord of the Rings. Players inhabit an imagined character, and one individual acts as the Dungeon Master (DM). The DM “runs” the game, playing the rest of the humans, monsters, environment, etc. In a way the DM is the game, the interface that channels the imaginary world to the players. A group of players is called a “party”.

When any one character wants to accomplish some difficult action: a feat of athleticism, attacking a monster, noticing body language that indicates someone is lying—they roll dice. Your character has attributes and abilities and equipment that may increase or decrease the result of the dice roll, which is compared against a difficulty score for the action. The DM describes how you succeed or fail the action, and the narrative resumes.

Your character can gain special abilities and equipment that allow them to perform a greater variety of actions actions: a wizard may learn to summon a fireball, a cleric may learn to heal wounds, a druid may learn to speak with animals. What powers a character gains are usually determined by their class, which is essentially a high fantasy archetype that you choose to inhabit: wizard, cleric, druid, etc. You track your characters attributes—their “stats”—on a character sheet.

The DM may choose to represent the space where the action takes place on a map with miniature figurines, but oftentimes this is only used for combat where precise positioning is relevant. The game is usually played over multiple sessions, and these sessions are referred to collectively as a campaign.

There’s a lot more to DND than just this brief summary, but as you’ll see I don’t find the minutiae very interesting.

The Dungeon Master’s Dilemma

I have spent much of my life playing the role of the nerd trying to lure unsuspecting normies into a marvelous fantastical adventure. I find myself drawn to the inexperienced RPG-player because they don’t have preconceived notions of what an RPG ought to be. This is important to me, because I think the enthusiast consensus has become that DND ought to play a lot like a regular board game, with predictable rules and legible systems. There are obvious reasons why this works for so many people: players love to optimize and express themselves via builds and synergies and strategies. I appreciate that they enjoy this, but for me squinting at stats and handbooks is a waste of an incredible opportunity to get some buttoned-up adults to feel wonder. You can get those optimization buttons pushed by a good video game or board game. To me the value of a TTRPG is not how it can resemble a board game, but how it can resemble a novel. Unlike a sterile set of mechanics, TTRPGs can have a sense of drama and pacing and character that no board game can ever approach.

Those who see DND as an aesthetic and setting to act as window dressing for their grid based combat game, I call ruleplayers. I prefer roleplayers, people who want to inhabit a character, explore a setting, live an adventure. That’s what draws me to the neophyte: I have a chance to try to craft them into a roleplayer—if their temperament allows—before the ruleplayers suck them in or wash them out. A ruleplayer sees failure during a campaign as bad luck, bad strategy, bad preparation, or unfair DMing. A roleplayer sees failure as a necessary source of conflict for a compelling narrative, or as an opportunity for character development and introspection. It’s a much more fun way to play in my opinion—given your DM understands the ingredients of good narrative—because you really open up the graph of potential universes when you include failure as a valid node.

But I can’t just hold to this desire for roleplaying over ruleplaying as dogma. The worst mistake a DM can make is bringing strongly held opinions to the campaign and treating the players as passengers or playthings. DMing is a performance art; a failure mode that performers tend to fall into is treating their imagination and preferences as a priori interesting. You experience your own fantasies in far richer color than you can relay to others because your brain is doing a lot of secret effort to fill in the blanks, and that doesn’t successfully come through when you put it to paper. People can grow to love the world you have built and the plot you have planned, but only if you meet them halfway and ultimately view yourself as a servant to your players, not a master (despite what the M in DM stands for).

Your players are coming to the game with different ideas for what they want from an RPG. This is where I reach for my 5th edition Dungeon Master’s Guide and let it fall open to my most visited page, Know Your Players.

I can’t quote it in full here because the text of the book is copyrighted (and too long). In brief, the section presents 7 motivations you should try to detect in your players: Acting, Exploring, Instigating, Fighting, Optimizing, Problem Solving, and Storytelling (I have been told the updated 5th edition adds Socializing as well, which I think is an important addition).

You need to craft your game experience to cater to these motivations, or you risk losing someone’s interest. Sometimes you need to be discriminating about who you allow into your group in the first place, because it will be a source of tension if you are trying to compromise between too many styles at once, especially if somebody is very obstinate about playing things their way and not willing to match the vibe of the group. The roleplaying blog Deeper in the Game has developed an exercise called the Same Page Tool to address these mismatching expectations, which they describe as a fundamental problem that ruins games:

Games work on a very simple principle- a group of people agree to a set of common rules.

Much of the problems in the hobby are rooted in failing this fundamental concept.

Imagine if you sat down with your friends to play “Cards”... one of you is playing Poker, another is playing Hearts, and the last person is playing Go Fish.

You’re all playing cards, right?

It’s not going to work. No one is going to get the game they want. The problem is that no one agreed to a common set of rules and no one is organized with each other. The common group activity that makes anything a game, doesn’t exist.

You don’t see this with cards because everyone understands you have to be playing the same game for it to work.

But you see that in roleplaying all the time... the key problem is a majority of the rules sets aren’t actually games. They give you rules to put scores to characters, resolve some fictional events but no larger picture. It’s like having numbers, faces and suits on cards- useful tools, but doesn’t actually organize what makes the game. What are the roles of the players? What is the goal of play? What is the intended play experience?

...Most of your “problem players” are just people who want to play a different game and are either under the illusion that you were playing a different game to begin with, or that different games could be mixed. This is why you see so much talk about the process of “forming a group”- it’s a process of trial and error trying to find people who want the same game as you.

I think anybody who is serious about offering their group an enjoyable experience is being dangerously negligent if they don’t do the Same Page and Know Your Players exercises, and foolhardy if they aren’t willing to walk away if the group makeup is too fractious. Most DMs that I have met don’t seem to have the maturity to give up their dream of finally introducing an audience to their handcrafted world. Those individuals spend a lot of time trying and failing to get people to play their games, because they are failing to give players what they want. From the same article:

Fun is reliably had when people are doing what they want to do- not because they’re tolerating it to please their friends, not because they’re secretly hoping for another activity, not because someone else is trying to “show” or “convince” them.

You cannot make anyone, including yourself, like something they do not like.

When people make that agreement and put in effort to make things work and don’t receive the expected play experience, whether the result of clarity, a lack of communication, miscommunication, or out and out misrepresentation – they get frustrated. With time, that becomes resentment...

Human nature is such that we operate on the assumption of an implicit agreement- a social contract, whether or not we actually sat down and discussed things. Regardless whether the group sat down and started “trying to play cards”, or actually agreed to a set of terms, when those expectations are broken, the feeling is betrayal, and eventually, complete distrust with repeated violations of those expectations.

Trying to hide the rules, not talk about the issue, or lying about how people feel or how the game works doesn’t fix the problem – at that point it feels like betrayal because it is.

I weep for everyone who got permanently turned off of roleplaying because their first experience was with an incorrigible DM or a mismatched group. It’s really the only type of game that can be literally whatever you want it to be, and yet it still consistently fails to live up to expectations.

The Social Skills Gap

Roleplaying, owing to its fantasy pedigree and proximity to make-believe, is still not generally seen as a dignified grown-up activity (except when you do it with your therapist). When a hobby gets exiled to the barren wastelands outside of the Overton window of respectability, only the people who have already bitten the bullet that they aren’t going to live in fear of society’s judgement will come near it. We call these people nerds. Nerds are a wonderful, guileless collection of humanity. Their only sin is allowing their enthusiasm for some thing to overtake their enthusiasm for maintaining appearances.

Many non-nerds have some secret passion or hobby that they only reveal once they’ve grown to feel safe with you. Nerds on the other hand tend to meet their friends primarily via sharing these hobbies with each other. In nerdy spaces and events, this creates a certain… dynamic. If everyone is there for the thing rather than the people, the people tend to not feel as much pressure to socially “perform” and you might get to witness some of the stereotypical nerd sights and sounds: passionate arguments over inconsequential subjects (rules or waifus), slovenly dress or poor hygiene, letting one’s passion for the hobby eclipse the duty to treat others with kindness and charity (the dreaded nerd rage).

I am not alleging all nerds are unpleasant, or even most nerds. But I have experienced a higher base rate of regrettable interactions in these spaces (and I think the nerds would actually mostly agree, but getting to live their truth makes the downsides worth it). Tanking them is generally just a matter of mindset and good humor. You must steel your nerves before venturing into the Dragon’s Den (your local board game shop), you must remind yourself of your love for all mankind before you descend into the Underworld (the Hell themed convention). But I love the nerds and I wish I was more like them: authentically myself and uninterested in the preening concerns of the neurotypical.

But my ideal TTRPG experience tends to require some high EQ. Collectively exploring your imaginations and fantasies while inhabiting characters in a shared delusion is an extremely vulnerable position to place yourself in (I imagine it’s sort of like taking shrooms together), especially if you have not yet successfully cast off the yoke of social expectations. Anybody who rolls up to this tender moment without excessive regard for everybody’s feelings or sporting a poor ability to catch on to social signals… they’re gonna destroy the vibe. The delicate dynamics of good roleplaying are so easy to wreck by not picking up on subtext and body language. The nerds already figured out their own solution to this: just make it as nigh unto a video game as possible, with systems and stats and strategies and figurines. When it comes to plot, stick to tropey high fantasy with unchallenging genre expectations. It works well enough for them, but I feel stuck on the outside. Almost nobody I want to play DND with wants to play with me because it’s a yucky game for weirdos, and almost everybody who would want to play with me is either a ruleplayer or otherwise misaligned with my motivations.

Forming a Party

If you still want to plunge into the exciting world of roleplaying, some thoughts from a fella who has spent some time playing and even more time thinking about how one ought to play:

Are you absolutely sure that you want to be the DM?

Being the DM is an attractive goal for many newer players. Your role in the group is objectively special and high status, you have a chance to get ideas that have been banging around in your head out in front of other people, you have a much higher degree of control and authority (I have mostly DM’d, and my main reason is that I trust my ability to tune the game’s vibe to the players more than I trust other people to tune the vibe to me. Judging from the preceding 3000 words, I think a lot about this subject and I find that most don’t).

You must be brutally honest with yourself: is this really what you want?

Have you had a chance to observe and critique other DMs’ styles? Actual Play shows like Critical Role and Dimension 20 don’t count and can even be actively misleading—the players are all professional performers and creatives and you will never be Matthew Mercer or Brennan Lee Mulligan.
Do you have a solid grasp of creative writing so you can competently plot setups and payoffs?
How are your acting skills? Do you feel up to the task of immersing your players in a world and embodying a diverse set of characters? Are you going to be embarrassed doing weird voices?
How are your improv skills? How quick are you on your feet? Are you ready for the stress of racing against your players’ encroaching boredom, trying to keep their attention over a multi-hour session?
Do you realize just how many hours of schlep await you before each session? A good hour of DND takes multiple hours to plan. This can add up to hundreds of hours of work over a campaign, with no guarantee that your players will even enjoy it.

With the right person DMing for you, being a mere player can be infinitely more enjoyable. You get to just show up and experience the fruits of somebody else’s labor. Counterintuitively, you enjoy a higher degree of agency as a player, as your actions are less bound by the expectations of the group and the constraints of the plot. Who has more fun, the guy who makes the video game or the guy who plays it? Well, which one has to get paid to do it?

Optimize for Existing Relationships

Since roleplaying is such a vulnerable endeavor, it can be tempting to try to do it with perfect strangers, or to utilize it as a way to meet new people. I think this generally does not work as well as you’d hope because of the reasons enumerated in the Same Page Tool quotes from earlier. Preëxisting trust and social capital help grease the wheels for a frank conversation of what kind of game you’re all playing together. A feeling of familiarity and safety helps you cut loose and play some make-believe.

I also think roleplaying represents a way to deepen or explore longstanding relationships that you may feel have reached a terminal state. Once you’ve known someone for a couple years, they can stop surprising you. But when you both stop playing yourselves and become somebody else, you can come to realize what you take for granted about each other, what you like and don’t like about each other. There’s a reason people roleplay in therapy!

Collaborate as Much as You Can Stand

I think a big mistake a lot of groups make is having everyone brainstorm their own special character and then all showing up and mashing them together. It starts a campaign off on the wrong foot when the first session meet-cute between the party members is disgustingly contrived. And it generates continuous friction when the characters don’t mesh with one another or with the setting or the story. A good group has players not only filling complementary mechanical roles (the healer supports the tank) but also complementary narrative roles (there is only one Tony Stark in the Avengers, not seven). This means the character creation process should involve the DM to some degree, as they can offer guidance about the setting and story, as well as bringing their creativity to bear to prompt less imaginative players.

The road goes both ways. A good DM is always open to hearing a player’s ideas for ways to shape the plot around their own character’s arc. Everyone should come away feeling like the protagonist. And even more importantly, a good DM listens to and solicits feedback. You want everyone to have a good time, and that requires fearlessly owning up to what doesn’t work and optimizing for what does, even if it doesn’t match your preferred style. When it comes to taking Ls, better you than them. Servant leadership.

A good group composition usually has at least one moderately experienced player for every two newbies. The DM can deputize them to assist others with fiddling with their character sheets, finding stuff in the rulebook, remembering obscure rules, etc. They also will “get” roleplaying in a way that helps the others ease into the grooves and rhythms of the game. The DM will be stretched thin in a room full of newbies, and the inter-party interactions will be awkward.

Experiment!

Stereotypical DND can be really dry and repetitive. You go to various locations, collect quests and plot hooks, descend into dangerous areas fraught with enemies and loot, get in a lot of combat encounters, and come back victorious and leveled up. It gets old. You can somewhat alleviate this by making the episodes believably feed into a grand story, but that’s often not enough. If you read enough about acting, creative writing, or game design—and you should read up on all three to be a better DM or player—you’ll learn that the greatest narrative lubricants to engage someone are spectacle (also known as crunch, presence, or payoff) and mystery (also known as subtext, depth, or setup). As a DM there are a ton of arts-and-crafts ways to dip into these twin wells of psychological manipulation.

Spectacle:

Thematic Music
Illustrations. I had my wife draw the party members once.
Cool things to put on the table like maps and miniatures
Costumes and props. Don’t go too crazy with these, their effort to payoff ratio is thin.
Physical minigames or puzzles
Handmade cards or tokens to represent game concepts. I think ruleplayers would go crazy for a DND variant where all of the loot and weapons were represented with MtG style cards.

Mystery:

Visibly taking players aside or whispering to them or passing notes
Discussing character motivations and narrative arcs separately before sessions so they can react to situations in surprising and narratively satisfying ways
“Accidentally” letting slip half of a secret
Hiding your rolls and calculations behind a DM screen
Secretly giving players abilities or items that they can reveal to the rest of the party at a time that feels right.
Giving somebody a scrambled or encoded message and drip-feeding them clues or information to decode it

Just phoning it in is eventually going to lose your party. A little bit of effort goes a long way to keep things fresh and exciting. I found my favorite trick was to hand everybody a note (written in a literary prose voice, like a paragraph from a novel) at the beginning of most sessions that told them something that had happened “off camera”, and possibly some editorializing about their character’s state of mind and goals. It helped gently guide their actions during the session and left them wondering about the others’ secrets. Your mileage may vary with this though, you need players that would appreciate that small erosion of agency instead of bristle at it.

As a player, there are also ways you can utilize spectacle and mystery. I won’t do another long numbered list, but it’s a lot of the same stuff: bringing visual aids, secretly scheming with other players or the DM, surprising heel-turns and heroic sacrifices. As long as you put in some effort to set up the dramatic moment for your character, it will be exciting and satisfying for all.

Roleplaying is a fun social puzzle: how do I craft an engaging story, while collaboratively leaving room for others to do the same? How do I convince respectable adults to play make-believe together? I think there are some deep and meaningful reasons behind why TTRPGs classically operate with larger groups rather than 1 on 1. There’s something divine about a shared experience and playing off of one another. It can truly be some of the most fun and satisfaction any hobby can give you.

It can also frequently be frustrating, boring, uncomfortable, exhausting, and confusing. But it doesn’t need to be. All it requires is some planning and some realtime adaptation, and everyone can experience a level of narrative freedom and immersive interactivity that is unprecedented.