Chaotic players can sometimes make you feel like your game is falling apart.

I have a pet theory that every adventurer will, at some point in their Dungeons and Dragons career, castrate a troll. I’ve heard enough anecdotes over the years about players wielding some poor troll’s severed member like a floppy meat-dagger that it almost feels like a rite of passage, like buying your first car, but with more bloody torture. Even if you haven’t experienced this precise scenario before, you’re probably imagining something similar that happened in your own game. Perhaps one of your players plucks the eyes out of everyone the party kills and stashes them in a bag, or keeps trying to kill enemies by conjuring an egg in their mouths, or torments his party members with magical bagpipe music.

All of those were the same player. We’ll call him “Dan,” because Jarret might be upset if I used his real name.

We sometimes derisively call this kind of play “Chaotic Stupid,” but I think it’s more fair to say that it’s just plain chaotic. It’s not good or evil per se, and it doesn’t even have to be stupid, but it is almost always unnecessarily complicated or illogical. To me, it is indicative of someone at a specific stage of player development: they’ve recognized the wide expanse of things that you can do in Dungeons and Dragons, but they haven’t given much thought to what you should do.

To be fair, ridiculous in-game behavior is usually played for humor. Like most jokes, however, there’s a time and a place for it. Too much of this kind of play quickly makes other party members frustrated. After all, it’s difficult to get anything done in a session when one or more players are just in it for the lulz; silly antics can be both distracting and time-consuming. Mounting frustration can turn toxic, and it can sink a playgroup if you’re not careful. At the same time, levity and jokes certainly have a place in Dungeons and Dragons; the multiverse is often a deeply silly place.

Players like this aren’t necessarily a problem, but you do need to work with them to keep your game on track and your playgroup happy. If you have a player or players like this in your group, I’ve developed a few positive strategies that you can implement while planning your sessions that will hopefully keep things fun for everyone, chaotic players included.

Establish Consequences (or, Play Stupid Games, Win Stupid Prizes)

One of my players is a wizard; more specifically, he’s a conjurer. Conjurers can, to a limited extent, summon small items at will. This player has decided to use this ability to conjure fake gold; fake gold that he then tries to use at every shop he walks into.

You may be wondering if this is Dan. It is.

It was funny the first time; now, I’m fairly sure that he does it just to get under my skin. That said, I’m not a big fan of telling players that they can’t do something that, mechanically speaking, they can do just because it annoys me. Instead, I decided that if fake gold is really easy for Dan to make, then it’s also really easy for other people to detect. Some shopkeepers have special eyepieces that can spot magical gold; others know that fake gold doesn’t taste the same as the real thing when you bite it. In any event, people are never happy when they realize that Dan is trying to rip them off.

Dan has been thrown out of shops, refused sales, and threatened with arrest because of his antics. He knows that if he tries something, there may be negative consequences for him, but he’s free to try it anyway. Remember: just because a player wants to do something weird doesn’t mean that they get away with it. But it also doesn’t have to be a source of irritation to you. I have a lot of fun roleplaying indignant shopkeepers, bouncers, and city guards as they unceremoniously toss Dan out on his ass, and Dan loves trying to make his grift work just one more time. Baking consequences of chaotic behavior into the game keeps the pace up and keeps the mood light.

Most chaotic players don’t want to piss you off; they just want to know what the proverbial big red button does. Let them press it.

Plan for Moments of Whimsy

Much ink has been spilled over the years about how to balance combat, exploration, and social encounters in Dungeons and Dragons, but there hasn’t been nearly as much discussion about how to balance tone. Just as players have a preference for different kinds of in-game interactions and objectives, they will also have a preferred style of setting. One player may prefer a completely straight-faced epic fantasy setting like Lord of the Rings, while another might want something more like the absurdist magic of Discworld. Most players will fall somewhere between the two extremes. As a dungeon master, it’s your job to balance levity and gravity. If you don’t, your players may “course correct” and do it for you.

One way to ensure that your players don’t run off in search of trolls to castrate is to create “moments of whimsy,” pre-planned set pieces that are primarily meant to be funny. In my own game, I have a shopkeeper named Felrazz Thistlepint, an old gnome who runs a scroll shop called “Thaumaturgical Tomes.” He has coke-bottle glasses, wild white hair, and a voice like Brad Neely performing Wizard People, Dear Reader. The shop itself is a rabbit warren of loose papers, books, and scrolls with stacks fifteen feet high. The shelves are so tall that Mr. Thistlepint uses a special harness attached to a rope-and-pulley system to move around the store. If that seems ridiculous, that’s because it was meant to be. And do you know who loves Mr. Thistlepint? Dan. Dan loves Mr. Thistlepint.

Memorable moments of silliness will keep players with a more chaotic bent from acting out. There’s less need for them to force more humor into the game if you’re already bringing it yourself. What’s more, you are respecting their unspoken request for the game to be a little less serious, and those efforts are almost always appreciated.

Encourage Player Growth

Most chaotic players don’t stay that way forever; eventually, they will figure out how to interact with the rest of the group in a way that is more productive than disruptive. As the dungeon master, you can help shepherd this process by putting players in situations that encourage emotional growth in their characters.

Dan, when he wasn’t running grifts, often talked about his character’s estranged son, Jasper. So, after about a year’s worth of sessions, I brought Dan face-to-face with his son. They had a direct confrontation that went very poorly for Dan, and Jasper banished him from the city. Afterwards, Dan and I had a conversation out-of-game where he said that he had long suspected that his conjurer was emotionally irredeemable, and the confrontation with his son only confirmed it. I devised a way for him to gracefully exit the campaign to make way for a new character Dan had created, one with a personality and backstory designed to be as unlike the old conjurer as possible. Dan wanted to grow and do more interesting things as a player, even if it meant writing off his old character to do it.

I must emphasize that I do not think that chaotic players are necessarily “problem players.” They can be, if their antics get in the way of other peoples’ good times, but most players like this, Dan included, are just looking to shake things up in the name of fun. To the extent that you can be adaptable, you should be. I’m not saying that you should put Sauron in clown makeup and a red nose, but you can tell a story with gravitas while also embracing the Merries and Pippins of your setting.

After all, you have to be flexible as a dungeon master, and what promotes flexibility more than a touch of chaos?

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