5 Tips on How to Design Diabolical Dilemmas
Posted by: Jendor -- August 21, 2014


by Johnn Four

I am not an expert on moral or ethical studies. But RPT reader Philip Wolfe asked for tips on how to add interesting moral decisions to his game, at behest of his players.

I feel moral dilemmas are the bread and butter of RPGs, because our games are often about good vs. evil. We all have a sense of right and wrong. Question is, how do we turn that into great gameplay?

Here are a few tips on how to give your game great dilemmas.

First, Philip's email to me (bold parts are mine):

Hey Johnn,

I really liked your recent list of Campaign Seeds and I'm about to start a campaign. The players say they want to see moral decisions or judgment calls in the new game.

I looked over a few of the lists of encounters you've sent out and they have been great, but not usually a moral decision. They seem to revolve more around mystery or "How do we solve this problem?" rather than "What is the right thing to do?" if that makes sense.

One of my all time favorites of your letters is How to Create Blockbuster Box Office Hits and I've laid out the overarching plot of the campaign I think will be the most enjoyable. But I also want the players to feel like they have significant choices that impact the rest of the game. I want to avoid them feeling like they are just walking down a path I've laid outfor them.

I want the players to be faced with moral decisions and judgment calls that really make the players feel like they are what the story revolves around. Suffice it to say I've faced two main problems:

1) It's difficult to come up with interesting and original moral or judgment calls that make the players feel significant. I have a couple but I've spent a lot of fruitless time trying to come up with more.

2) If those choices are really that significant, how do I prepare the plot and story for any choice they could make? I think a good moral decision could appear only to have 2 choices but truly has many more.

At any rate thanks for reading and any advice would be great.

[Johnn: I replied to Philip and asked him for some example moral situations, just to see if we were on the same page. His next response is as follows:]

So part of my dilemma is coming up the situations. Do you have any advice for generating these situations? I don't feel like they all impact the overarching plot of the game but perhaps that is not necessary.

I did my best and got 10 together that I think would be interesting:

  1. The King or other legal authority sends you on a mission to track down and apprehend a war criminal. When the party catches the criminal he pleads with them saying he is innocent and he will never get a fair trial. He then provides moderately sound proof he is innocent.
  2. When one of the players does something drastically illegal and gets away with it, they find out a little while later an innocent person has been caught and has very good evidence against them for the crime. Does the party use this person as a scapegoat?
  3. The party is provided with a valuable, yet fragile artifact in a city. Only moments after they procure it a young child snatches it and runs away with it. How much force is the party willing to use on this child to get it back?
  4. When lives are at stake with only a certain amount of time to complete their goal, the party comes across a family on a pilgrimage. The family has something that would save days if the party had it. However, the family refuses to trade or sell it because they need it to cross a lake or mountain pass. Without it their journey would take several weeks more.
  5. The PCs find a child holding nothing but a small knife out towards a pair of vicious animals. If the players intervene the child calls out for them not to interfere. The child provides no explanation but only pleads with the players not to help him and he has the situation under control.
  6. A man is yelling at a woman calling her all sorts of obscenities and gripping her by the shoulders. She looks frightened and ashamed. He starts shaking her. If asked if she needs help the man shouts they are fine and to mind your own business. The woman shakes her head with frightened and pleading eyes.
  7. A known terrorist and fanatic has been apprehended. It is believed he has several bombs set to detonate sometime today. He refuses to talk and demands his lawyer. His daughter and wife are also nearby whom he clearly cares for. What are the players willing to do to save hundreds of lives?
  8. The players are under the command of an officer and they have been tracking a criminal. When the party finally finds the criminal and disarms him, the commanding officer orders the players to kill him saying he is too dangerous to keep alive and that he has already escaped their detainment several times.
  9. Time is of the essence and many lives are at stake. While the party gets closer to their goal a passerby pleads with them that his young son has run away from home in search of adventure. There are dangers everywhere and the boy ran in the opposite direction the party is going.
  10. A PC is caught alone with a woman with murder in her eyes. She holds out a weapon and demands the PC yields his money. The PC then notices the woman is pregnant.

Here are some tips that hopefully help Philip and you create moral dilemmas in your campaigns.

1. Create Situations, Design For Gameplay

First let me call out this is all in the context of gameplay. We are aiming to design something interactive and making a game of it. We're not writing the news, writing a script, or authoring a book.

So our first goal is to create situations where possible and unleash them. All we can do is bring the players to the dilemma, and then we have to let go, lose control.

We might be tempted to build out a sequence of situations that compress the crucible and heat things up for the PCs. But we can never depend on a chain of events, because players get to choose their characters' actions, starting with the first fork.

No point, then, going the traditional media route of planning cause and effect over a timeline. It's bad gameplay. La railroad.

Therefore, I first recommend getting a good idea of what ethical dilemmas are, in general terms. Attune your spidey senses to spot opportunities in gameplay and in your Loopy Planning for potential dilemmas. This is a skill, and takes practice.

Create Situations

We benefit from having anything not yet made known to players remain in flux, and we can amend such things on the fly to pivot them into moral dilemmas. With a growing skill at spotting these opportunities and making the most of them, you'll level up as GM.

For example, item #1 on Philip's list - the war criminal. Say you had this plot planned from the start of the campaign. But before you introduced it, last session the PCs made friends with an NPC running an orphanage. He actually hired them for a quick job to find a missing child.

Next session it's time to trigger the King's quest for justice. Your spidey senses tingle, and you realize you can tie the orphanage stuff to your plot idea. You could make the NPC running the orphanage the war criminal. Or you could make the NPC who's funding the orphanage the criminal.

Now the characters will have to choose risk to the orphanage or justice.


More ideas pop into your head. What if the NPC has a twin, and the wrong one gets caught and convicted? Or what if the NPC displays much remorse while being hauled back to the King? Or what if the NPC saves the PCs' lives - now they owe him one. Or what if the "war crimes" were actually moral? What if, what if....

We can use these ideas because they're backward compatible and they do not contradict the fiction we've created so far.

However, while these are interesting ideas, resist the impulse to chain them together. Set the table for the first encounter, and let the PCs make their first decision. You react to that and setup the next encounter.

Meantime, you look for ways to tie things together (or break them apart) to create or enhance dilemmas. We're not writing scripts, just playing with Lego.

Design For Gameplay

Next, look to your game rules and character sheets for PC opportunities to use skills and abilities to roll some dice.

If your group roleplays, you're looking for opportunities for debates vs. plan-making (that means you'll need NPCs in play).

And you're looking to create decision points. But not just regular decision points => you want to build up to excruciating ones.

For example:

Scenario A: The King hires the PCs to track down a war criminal. Standard quest. After several encounters, the PCs find the guy, bring him back, and get a reward and XP.

No decision points here. You need to add them. You need to add an alternate version of reality or perspective to get the dilemma machine whirring.

GM Level 1.

Scenario B: The King hires the PCs to track down a war criminal. After several encounters, the PCs find the guy. He says he runs an orphanage. The PCs chat briefly, and turn him in anyway.

We created a moral dilemma and decision point here, which is great. Orphans vs. justice. GM Level 2 unlocked.

But we can do better.

Scenario C: The King hires the PCs to track down a war criminal. After several encounters, the PCs find the guy. It's the kind old man they met awhile ago who runs the orphanage! "Snap, what do we do now?"

This stirs things up better, because we've added on-the-fly an NPC the characters have already met and built some respect for. He's known and liked. Our original plans were for a new NPC to be the criminal. But we saw a way, either in the moment or between sessions while planning, to add a twist and re-use a game piece to create a dilemma.

And we can do this because there are no logic errors or fiction issues with what the PCs and players know. Sure, we initially planned things one way. But if you are a new GM, you might not realize you can mashup things to suit your purposes anytime as long as the game stays consistent and the fiction remains unbroken.

GM level 3 achieved.

But we've really only setup a debate, some great roleplay, and a tricky decision. How can we run with this situation to create more gameplay? Now is the time to add in your first idea.

(Sidebar Tip: Implement each idea in a new encounter. Instead of just handing your idea out, mix it into another encounter, like how I'll add chocolate chips to almost any cookie recipe. Can't hurt, right? :) Every encounter propels gameplay. So, if you turn elaborating on your dilemmas into spawning new encounters you are expanding gameplay.)

Scenario 4: The King hires the PCs to track down a war criminal. After several encounters, the PCs find the guy. It's the kind old man they met awhile ago who runs the orphanage! "Snap, what do we do now?"

The PCs decide to take him back anyway, and be character witnesses (ha! pun not intended) to help the NPC plead for leniency. On the way back, you trigger your first idea: reveal the war crimes were actually moral.

We can do this because in our scenario the King has not actually told the PCs what the war crimes were. We can make retroactive changes as we see fit as the gameplay develops.

(Sidebar Tip: keep your cards close to your chest, as they say. Dole out only what information the PCs need and ask for. This gives you more latitude to adjust gameplay in-progress. Also, position facts and information with wiggle room. Do not make everything an absolute certainty. Instead, hand out in-game information through NPCs, scrolls, and other in-game means that could be wrong. This gives you more wiggle room to execute your ideas without breaking the fiction.)

En route back to the kingdom, the PCs encounter a pack of fire yeti. Combat erupts. A yeti nearly kills the NPC with a vicious claw strike to his neck. The NPC screams, "Please save me! Yes, I'm guilty of war crimes. But it's not what you think. I saved a village from my evil army!"

We've revealed the twist. We decide the NPC was in charge and his men started pillaging a village after defeating the rebel defenders. The NPC stepped in and had to attack several of his own men to save the village. He was taken prisoner, but then escaped and helped the villagers flee to safety.

A war crime worthy of torture and hanging for the NPC? It's up for the PCs to decide now, if they believe the NPC.

We could have shared this story when the PCs first caught their prey. The NPC could have told the whole story. But we want to create more, interesting gameplay. When the yetis attacked, an encounter you did have pre-planned, you saw an opportunity to deepen the dilemma. You had a yeti attack an NPC - always a good practice for believability and drama. You rolled, the yeti hit, and you saw a way for the NPC to share more of the story.

GM Level 4 achieved.

It could have gone a different way, with the PCs making their perception checks and avoiding or ambushing the yetis. The NPC doesn't get attacked, and can't plead for his life.

I'm talking about the way I actually run games here, this is not theory. And when I have a desire to see the game go a certain way - "Hmmm, wouldn't it be cool if the war crimes are not evil, and the NPC reveals this while fighting for his life under PC protection battling these fire yetis I've got queued up?" - I pull what levers I can to make this kind of stuff happen.

But if the players make confounding choices, or the dice take the game in another direction, I do not force my ideas on gameplay.

I think this is key to being a better GM. You need confidence and patience. Be confident you can execute your idea in some other way next encounter, or the encounter after that. Be patient so you don't force your ideas into encounters so gameplay feels contrived.

Also, you always have trump cards. As GMs, we have the whole world at our disposal to bail us out. If everything fails - the PCs thwart the yeti too fast, other encounter opportunities fail to manifest, the PC wizard catches the NPC by accident in a fireball and kills him - if everything fails we've always got more levers.

For example, NPCs are always an option. I could have an ally of the NPC come to the PCs after their return and plead the NPC's case and ask they break him out of the dungeon. What if the ally was a group of orphans? "We don't know what will happen to us if he's hanged, misters. We'll probably be sent to the mines! [Insert tears falling down cherub cheeks.] We know he's innocent! [Reveal part of the truth here.]"

So I think attaining higher GM levels involves being patient and confident, and using the levers at your disposal to generate dilemmas through gameplay.

And don't worry if you can't think fast on your feet. Do what I do and write down your ideas. When stumped, I refer to my ideas list and Loopy Planning document to see what game pieces and levers I can employ to create the next encounter. Or, if the players are generating the next encounter, not me, then I'll review my notes for ways to enhance the encounter to further my agenda.

2. Compel PCs to Act

Wikipedia says a moral imperative is "a principle originating inside a person's mind that compels that person to act."

In terms of gameplay, every decision needs a consequence. Introduce these consequences during the decision point to make player choices truly difficult.

Pick one of these approaches and fill in the blank:

  • Threat:: Make the worst choice or else ______."
  • Loss:: If we choose Option A, we lose ______. If we choose Option B, we lose ______."
  • Evil wins:: If we choose Option A, evil wins because ______. If we choose Option B, evil wins because ______."
  • Good loses:: If we choose Option A, good loses because ______. If we choose Option B, good loses because ______."

Another angle is to consider these questions:

  • Who gets hurt?
  • Who escapes justice?
  • Who undeservedly benefits?

Most important of all, though, is to complete your plans with this statement:

"If the PCs do nothing, ________ happens."

No four letter words in the blank, please. :) Insert some bad effect on the PCs and their world, and then work into gameplay this knowledge so the players know what's at stake.

Downstream Effects

In addition, always consider who gets affected by the PCs' choices. Look at the downstream effects.

If the PCs go one way, how does that affect the villain, the party's allies, and innocents? If the PCs go another way, what are the effects of that?

Try to make these effects important to NPCs key to your story. If you can ruin the villain's parade, you have fantastic grist for response, if not retaliation, which means opening up more great gameplay. Likewise, allies who get screwed over will react. And innocents caught in the middle just gives you more dilemma opportunities.

As the story progresses and you confront the players with new choices, compel their action by pondering the consequences of their potential choices and making these known to your group, ideally again in-game via roleplay.

"We don't know what will happen to us if he's hanged, misters. We'll probably be sent to the mines!"

Learn From Pain

If the PCs make a bad choice but they tried to make the right one, game out the consequences, but not in a punitive way. If the Orphan Master gets hanged, send the orphans to the mines. Hopefully the PCs take it upon themselves to rescue the children.

But if the players blow off dilemmas, be murder hoboes, and be corrupt, then reveal to them later in the campaign the consequences of this behaviour. And keep deriving unfortunate gameplay from their previous decisions.

Make it so the PCs' past selves keep sneak attacking their present selves.

For example, not turning in the Orphan Master means the group loses the 500 gp reward. So they throw the guy at the King's feet and demand their money. The orphans turn up and plead for help. The PCs extort another 500 gold from orphanage coffers and agree. They break the Orphan Master out of the dungeon, and lead him and the orphans across the border to start up anew. Then they sell this information to the King for a small 100 gp reward.

All in all, a profitable week for the rat bastard party.

Next week, the Captain of the Guard finishes his investigation and learns the PCs were the ones who broke into the dungeon and rescued the Orphan Master. The PCs are tougher than his guards though, so he posts a 500 gp reward for their capture for "war crimes". Tit for tat.

The week after that, the Church of Holy Light declares an inquisition on them. Divine agents start hunting.

Two months later, the Orphan Master and his group of thugs - fellow prisoners he took with him on his escape - make life miserable for the party.

You stage all this gameplay not out of personal vengeance, but as a logical and realistic consequence of party decisions. You decide how far you want to go with this, and what your group finds fun.

3. Turn Dilemmas Into 5 Room Dungeons

If you recall the standard 5 Room Dungeon format:

  • Room 1: Entrance And Guardian
  • Room 2: Puzzle Or Roleplaying Challenge
  • Room 3: Red Herring
  • Room 4: Climax, Big Battle or Conflict
  • Room 5: Plot Twist

These are metaphorical rooms. Use them to structure the great unraveling of a dilemma through gameplay. The format makes a perfect recipe to do this.

Drawing from Philip's examples again: "When lives are at stake with only a certain amount of time to complete their goal, the party comes across a family on a pilgrimage. The family has something that would save days if the party had it. However, the family refuses to trade or sell it because they need it to cross a lake or mountain pass. Without it their journey would take several weeks more."

Room 1: Entrance And Guardian

The PCs encounter the family. We need to reveal the thing the party will want. Let's say it's a well-crafted large wagon pulled by two impressive horses. The heavily-armoured PCs could hop on the wagon and party speed would double, and the indefatigable horses would mean longer travel days at forced march rates without party exhaustion.

So, we have the group come upon the family being shaken down by bandits.

Room 2: Puzzle Or Roleplaying Challenge

After the bandits are taken care of, the PCs can try to negotiate for the cart.

The family won't part with the cart. Well...they might if the PCs can help.

The family says the bandits attacked before, and they managed to steal a lot of their stuff. Can the PCs get it back?

Room 3: Red Herring

The party finds the bandit hideout - a ruined fort. There are several tough bandits there. From atop the walls, the bandits declare the PCs' mothers were hamsters and their fathers smelt of elderberries.

Inside the fort are all the family's stolen belongings.

Upon return, the PCs present the family's stuff. But the family realizes making haste on their journey is more important than getting their things back - even the sentimental items - and decide not to give up the wagon and horses.

Room 4: Climax, Big Battle or Conflict

Confrontation. The PCs must decide whether to take the wagon and horses by force or through trickery, or to let the family be on their way.

Room 5: Plot Twist

As the PCs travel onward, regardless of the outcome with the family, they encounter a village where another awesome wagon and pair of horses are for sale at a reasonable price.

If the PCs left the family alone, this is a victory. If the PCs robbed the family, this is a defeat.

Dilemma Ideas

Here are a few ideas and situations to help you generate some dilemmas.

Law vs. Good

Create a law that benefits society. Then create an NPC or faction where the law hurts or penalizes them.


  • You can kill drow and get a reward. What if one of the drow is Good? Flip it: by law you must kill drow upon sight, but what if you come upon a defenseless drow mother and her scared children?
  • People who steal to support themselves because they are not legally allowed to work.
  • Murder is illegal. The PCs, who have no legal authority, confront the villain who refuses to go with them.
  • Slavery is legal. The PCs come upon slavers mistreating their slaves.

Class Distinction

Your setting does not have to reflect modern morals.

Create a social class, such as Nobility. Give them privileges and things the PCs want. Give those privileges a dark side or give the classes looser morals brought to bear.

For example, wizards are a distinct class. What will wizards make the PC wizard do to get access to their libraries, equipment, and mentors? What will the PCs be willing to do for Remove Curse?

Another example, royalty. They can get away with all sorts of crimes, and might offer PCs lucrative commissions to do terrible things, with full pardons.

Faction War

The PCs' faction and another faction go to war. What atrocities will take place in the name of victory? And how will the party react?

  • The PCs are ordered to commit an atrocity
  • The PCs witness an atrocity taking place against their foe
  • Reports of atrocities made by their own faction reach PC ears
  • Foes commit atrocities in front of the PCs
  • A third party commits an atrocity against the PCs' foe

Revenge of the Dead

What happens when death is not the final stage of life?

Raising the dead, communing with spirits, souls travelling to the planes, and an undead afterlife are some plausible ways for the deceased to come back and haunt the PCs.

  • Will the PCs tell a lie to a dying friend to ease his last moments?
  • Will the PCs kill foes, knowing they'll soon come back in a stronger form?
  • Is killing not so bad, then?
  • Do you obey ancestors who can come back and kick your ass?
  • How does a society now regard death rights and sanctity of the dead?

Code of Honour

As we know, D&D paladins typically have a Do / Not Do list. If they ever break a rule there could be serious repercussions.

But you can create honour codes for any game system, any genre, any character.

Just make up a list of bad behaviour that'll be punished, good behaviour that'll be rewarded, and a couple bennies if game balance is an issue.

Character classes, professional, races, cultural traditions, and nationalities might all have honour codes a PC might inherit.

* * *

Creating moral dilemmas is tricky. If your players want such play, ask them to put some skin in the game by giving their PCs morals. Then create situations that challenge those morals.

Regardless of choices made, change the world. Have NPCs, factions, and even societies react to the outcomes of moral dilemmas. Then turn this into more gameplay.

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