Designing Dilemmas for Dungeon & Dragons

A dilemma is a choice between two undesirable alternatives. Dilemma is one of the most effective and frequently used tools in the story teller’s kit. However, it can be challenging to implement in a Dungeons and Dragons game. It is worth learning how to use dilemma in your adventure designs, despite the challenge.

The most important difference between a good adventure scenario and a bad adventure scenario is meaningful and interesting choices. Dilemmas are the some of the most challenging and interesting types of choices you can present to players. A properly designed dilemma will have your players squirming in their seats. A great dilemma will bring out an emotional response. A powerful emotional experience is what creates memorable events that players will talk about for years to come.

Dilemma in Stories

Dilemmas are the at heart of any conflict in stories of nearly every type and genre. The protagonists dilemma is what defines the theme.

In the 2002 film Spider-Man, the Green Goblin tries to make Spider-Man choose between saving a bus load of children or Mary Jane.

In the movie Sophie’s Choice, the eponymous Sophie has to make a terrible choice when she arrives at the Auschwitz concentration camp. She has two children with her. The guards will allow one to go with her into the labor camp and the other goes to the gas chamber. They make her choose.

There are also stories where the protagonist has a quandary in which both choices are positive but lead to very different outcomes. One classic plot is a woman being wooed by a man who is reliable but boring and another who is less reliable but exciting. One man will provide stability and be a good earner. The other promises be a lot more interesting but might end up living in a van down by the river.

Photo by Oliver Roos on Unsplash

Dilemma in Tabletop Role-Playing Games

Very rarely have I seen this technique used in published adventures or recommended to game masters. Typically, players are presented with a hook or a quest and they follow that bread crumb to the next point and to the next point and so on. I have frequently seen the illusion of a choice that amounts to: Pick the terrible thing or the game doesn’t progress. A lot of horror game scenarios offer this faux choice.

It is the rare designer who will create exclusive this or that choice nodes. A dilemma requires that once the choice is made, there are unavoidable consequences. It is a point of no return. It’s not a particularly efficient for a designer to create an adventure where half the content will not see play with a given group. This is one reason for reluctance on the part of designers to use this technique.

There are a number of ways you might employ dilemmas. Here are some of my favorite ways to create dilemmas in Dungeons and Dragons.This isn’t an exhaustive list. I recommend putting “moral dilemma” into your search engine of choice to get some ideas for scenarios.

Magic Items

Magic items are a great way to create a dilemma for your players. A low stakes version is that a character already has two magic rings. They find another magic ring and the rule is you can only wear one on each hand. Which two are you going to pick? You only have one head, you can only wear one hat or helmet.

I like creating magic items that tempt the user to abuse them in socially deviant ways. A magic item that has a powerful effect but one that is tempting to abuse creates conflict and dilemma without much effort on the part of the referee. The ring of invisibility can be terribly tempting to abuse. Put one in the hands of the thief character and the adventure creates itself.

Create a powerful object that has significant downsides. One of the players in my last campaign found a demon that exists in the form of living armor. Once you put it on, the only way to take it off is with a remove curse spell. It is ugly, disturbing to those around you but has powerful protective features. There is also the downside that if the PC dies while wearing it, their body and soul goes straight to the abyss.

Another magic item connected adventure is a job where the characters agree to fetch an item. The quest giver is willing to give them a lot of money for it because it is dangerous to go acquire but the item is very valuable. Once the characters get the item, I make sure they find out several important facts:

  • The item is very powerful.
  • The item comes with significant downsides if you keep it.
  • The item is incredibly valuable to more than one party.
  • The quest giver is probably going to use it for evil purposes.

If you are playing a game with XP for GP mechanic, there is massive incentive for the players to sell the item. I don’t give any XP for keeping an item. If an item is used in an adventure, there is no XP even if they sell it later on. If they do sell the item, it is likely to pop back up in the hands of an NPC later in the campaign. The player’s now have to deal with the consequence of the item they could have destroyed (for good) but decided to sell for selfish (maybe evil?) reasons.

Bad Good Guy Vs. Good Bad Guy

I rarely have pure “good guys” vs pure “bad buys” as major NPC’s in my settings. Most of my major NPC’s have a major flaw and are seeking to accomplish something that could be thought of as “good” from a certain point of view.


The great druid is adamant about protecting the forest, its indigenous people and the animals that live there. (Good) He’s willing to murder anyone, cause wars, unleash monsters on peasants, cause famine and disease in order to discourage settlement and drive out interlopers. (Evil)


A vivimancer who is mutating people and animals via magic in horrifying ways (Evil) He uses the results of his experiments to improve the yields of crops and animals to feed the growing population of his city and heal the sick and injured. (Good)

Both are far more powerful than the party and they demand you pick their side. Each one offers their own enticements and protection against their enemy. Maybe you choose a third way of your own devising to be “good” but that involves its own sacrifices.

Tactical Dillemas

Though I’m using the word “tactical” which indicates choices in combat; I also mean choices such as which way to go at a dungeon intersection. It is important that the players are aware:

  1. If they choose Option A then Options B and C are now closed to them.
  2. There is a significant and meaningful difference between the options.
  3. The players need to be aware of the potential award/punishment for making a specific choice.

Example: There is a fast moving and deep river the PC’s need to cross. There is no bridge. There is a pack of ghouls hunting them and they are close by. If they get across, the ghouls aren’t likely to follow. The options might be:

  • Try to swim it.
  • Send one person across with a rope to secure to a rock or tree on the other side for the others to cross. (Takes time, probably loose the rope)
  • Run down/up stream and find a safer way to cross.
  • Spend a single use magic item like a scroll or potion
  • Use a spell
  • Fight it out and then cross.

They don’t have any choice that is risk free or without a cost. The players have to pick between risking death or using a resource that may be more valuable further along.

Final Thoughts

Dilemma is a powerful tool but there can be downsides.

Making choices hard for players can slow the game to a halt. Take into account that if you make the dilemma too thorny, players can chew up a lot of time in debate. It can be a way to test the faith of a paladin or priest by tempting them with something that goes against the strictures of their gods. If the rest of the party is all for it and the paladin is forbidden, this can create problems. Carefully consider if you want that kind of conflict in your game. I recommend caution.

You don’t have to make the stakes life or death in every dilemma you create. They can be small. In fact, it might be good to keep most of your dilemmas with low stakes. They are points of no return. In order for a dilemma to be effective emotionally, there can be no take backs. Once the players pull the trigger, that is it. Which also means you need to think through the consequences of the choices. The players may choose evil. You have to decide whether you are willing to follow that path to its logical conclusion or not.

Take note of dilemmas in the media you enjoy. Write them down and use them as design prompts for your own games. A recent example is The Mandalorian. There are a number of dilemmas that the main character has to navigate in order to accomplish his goals. The writers did an excellent job of putting the character in situations where he has to choose between “the way” and what’s right or expedient for his mission.

I hope that I’ve convinced you that building dilemmas into to campaigns, adventures and encounters is worth taking the extra time and effort. Dilemmas can create incredibly dramatic moments that increase player engagement and immersion.

5 thoughts on “Designing Dilemmas for Dungeon & Dragons

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