This post may be of some use to people who want to insert ethical dilemmas into their games, or people who want their dilemmas to suck less.
What is a Dilemma?
If you punish your players whenever they do something bad and reward them whenever they do something good, YOU HAVE REMOVED ANY ELEMENT OF A DILEMMA FROM THEIR DECISION. If the players learn that the DM sends shit-tons of town guards after them each time they rob a hobo, they will stop doing it. If the players learn that they'll be given 2 healing potions whenever they spend a healing potion healing a dying hobo, they'll heal every dying hobo they come across. Congrats, DM! You've succeed at getting your heroes to act heroic all the time, but also managed to remove any morality from the heroics. It is now a previously-solved math problem, just a lever that your players must push in order to get the food pellet.
If a player doesn't sacrifice something to be the good guy, they aren't actually being the good guy, they're just the Randian opportunist guy who happened to do something good because it was to their own benefit. Or at best, a good guy who hasn't had his goodness tested.
"Will you fight evil or die when the evil conquers your country?" is an easy question to answer, and one that selfish assholes will answer the same way that noble knights would.
"Will you fight evil or live a long, happy life while bad things happen to other people far away?" is much more compelling, but also harsher because being a hero now has a cost.
So dilemmas are inherently about sacrifice (even if that sacrifice is just opportunity cost). You need to present multiple options where the difficulty lies in choosing what you value. Contrast this with (most) combat, where the goal is to choose the best way to get what you obviously value.
Anyway, here are five types of dilemmas, ordered roughly from least- to most-favorite.
1. The Untrustworthy Knight: Incomplete Information
A knight walks up to you and says that he needs you help to steal a thing to do a good thing. His armor is shiny, but is he a good guy or a bad guy? Will he use the thing to do a good thing, or is it really going to be used for a bad thing? Do you trust him?
These dilemmas are primarily questions of trust that force you to make a decision based on incomplete information.
That's why I don't like them, usually. At their worst, it's just the DM asking the players to make a blind choice, with a cost/benefit that is entirely unknown to the player. It's like giving them two identical doors, with sudden death behind one door and 1000 miniature horses behind the other, each wearing a golden collar.
Exception: These dilemmas might be fun if the stakes are low. Like, if you guess correctly you win magic pants that can turn into any other pair of pants, but if you lose, everyone loses their pants.
Exception: These dilemmas are a little better if that ignorance is part of the challenge that can be overcome (before having to make a decision). Like, you could get a head start on the job OR research your boss's history. Or you could choose the historical books as your reward instead of the bag of gems.
This type of dilemma is similar to when the DM springs a "Aha! You were working for the bad guy all along!" moment on you. Which is different, but usually still boring. (Better: Your boss is a bad guy who does bad stuff, but his job for you is good stuff, like bodyguarding his 8-year-old daughter from kidnappers. I love evil-but-friendly, or evil-but-not-doing-evil-currently).
2. The Undead Workforce: Do the Ends Justify the Means?
These are pretty common in freshman year ethics classes. Would you kill 1 person in order to save 3? Would allow 1 person to die in order to save 2?
The usually involve doing something distasteful in the short term in order to do something desirable in the long term.
This can be a utilitarian consideration (will you kill 1 to save 2?) or a Kantian one (lie to prevent a murder from ocurring?).
The classic example is farm-zombies. Lots of people think of raising undead as a victimless crime. Why not raise a bunch of undead and use them as a cheap labor source, in order to make the world a better place. (Protip: if you don't want your players coming to this obvious conclusion, you should invent a reason why necromancy isn't a victimless crime.)
Another nice twist is: players kill evil cult, players find out that regular sacrifices are required to keep even greater evil from awakening, and that the cult they just killed was keeping the world safe after all. (This usually ends with the players restarting the cult, fleeing that part of the world and never returning, or getting TPK'd by the demon they just unleashed).
These are also related to things that are "against a character's code". Like, would the alcoholic dwarf choose to save the baby or the cask of beer? Would the paladin allow a witch to live so she can brew an antidote to the poison that is affecting the village?
The problem with these dilemmas is that players often take the long, utilitarian view, and have no problem killing an innocent guy in order to save three children. (This is because they're abstracted from the game, and NPCs are more like symbols than they are like real children. Also, it might be possible that my players are atheist munchkins without pity or remorse.)
The trick is then to make the sacrifices more meaningful. Would they kill their favorite NPC in order to save three kids that don't even have names, much less stat blocks?
Alternatively, change the sacrifices to thing that are not easily comparable. Would you kill an innocent woman to save the Mona Lisa? Would you make spaceflight impossible in order to cure polio?
All this talk of comparing incomparables brings us to my next point. . .
3. Truth or Happiness: Choosing Between Two Goods (or Two Bads)
This type of dilemma asks you to choose between two things that are both desirable. Or, on the flip side of the coin, between two undesirables.
If you look close, this is pretty much the same as #2. Nominally, you could say that that this dilemma (a) is about making a single choice at a single time and (b) always involves incomparables.
Who do you support for king? The kind prince or the competent one?
Which society is preferred? Safety or privacy?
Now that you know that everyone goes to hell when they die, and there truly is no hope for anyone, will you report your findings honestly to Astral NASA, or lie about it for the sake of their sanity?
The difficulty here is that you are comparing incomparables, and those are always subjective. While you might think that safety vs privacy is a compelling dilemma, your players might spend 0 seconds debating, because one of those option is obviously far better than the other.
If that happens, don't sweat it. They interacted with your world and made a choice; that's all you can ask for. They may be patting themselves on the back for making the right choice so quickly.
4. The Beloved Wife: Mechanical Advantages vs Fictional Rewards
Alright, you got me. This is just a sub-type of #3. But it's a very special, very common type of dilemma, and so they get their own category.
The classic example is this: how much would you risk (or sacrifice) in order to save your beloved (and fictional) spouse?
These dilemmas ask players to choose between mechanical power (munchkin-ism) and mechanically-neutral awesomeness.
This dilemma actually happens all of the time. Whenever a player decides to kill+rob or not to kill+rob a random NPC, they are engaging in this dilemma.
Oftentimes, there's no mechanical drawback to murdering a wandering minstrel and taking his 3 silver. For the pure munchkin, this is no dilemma. Just kill everyone whenever you can get away with it and take all of their stuff. But no player (that I've met, anyway) is 100% munchkin. Most players would choose not to slaughter all the orphans. At least, not for less than 100 gold. You just need to find that break-even point and flirt with it.
And it's okay if your players don't always choose the option you want them to. That's them expressing their agency, deciding what kind of heroes they want to be. If you don't get this, then go back and read the section on "What is a Dilemma?"
And of course, there's glory. Glory with the big letters and the public acclaim and adoring fans. Will your character choose the 1000gp or a (mechanically worthless) title? Will they choose mass popularity or another +1 to hit?
Pride + awesomeness is a obvious Thing of Positive Worth, but what about shame?
Would you lick the mud off a balor's hoof in order to save the princess? (The balor isn't here looking for souls. It just want to humiliate and degrade the faithful.)
A certain kind of player (and DM) hates the idea of shaming their character as part of a moral dilemma. Isn't playing an RPG all about escapism? Isn't it about player empowerment? Isn't it about being a badass who is capable of saving everyone?
Sure, for some people in some games. But how much is it worth to you that your avatar is a Cool Dude? For some players, it's an interesting character question and a serious roleplaying challenge. Other players will be uncomfortable having to choose between two things that they thought were guaranteed when they signed up: being a honored badass and saving people's lives.
Just remember that if you want to incorporate humiliation (as a counterpoint to glory) into your moral dilemmas, please please please make it an option that the players choose without coercion. Don't be the heavy-handed DM that says, "Since you fail your Str check, you are now the roper's sex slave. Roll vs penetration."
If your player is willing to sacrifice their fictional self's public honor--their beloved power trip--in order to save the life of a fictional person, I think that can be privately honorable and impressive and heroic.
One of my favorite scenes in Trigun is when Vash humiliates himself in front of the bad guys in order to save some hostages without bloodshed. He runs around on all fours, barking like a dog while the villains mock him, and I thought he never looked more heroic. (Not everyone would agree with me here, but isn't that a point of a dilemma?)
Another example: what's better, shameful secrets and public acclaim, or honorable secrets and public shame?
And a shout out to +Courtney Campbell, who DMed the first (and only) game I've seen a player lick the mud off a demon's feet. It opened my eyes, man.
5. The Caged Demon: Open-Ended Problem
This last type is the broadest, most vague of all the types of dilemmas. You are given a problem without any obvious options and told to solve it. A major distinguishing characteristic is that, unlike previous types of dilemmas, there is a huge benefit to being clever (not just choosing between pre-described options).
A good example (semi-cribbed from one of +Gus L's games) is a coffin with a horrible demon inside it. You lack the resources to destroy the demon or the coffin, so you are tasked with disposing of it. You can't throw it in the ocean, because the demon would just summon ruthless sahuagin to it via dreams and be released. You can't just bury it underground, because it will call to dwarves in the same way. Lacking a convenient volcano, what do you do?
I don't know. This dilemma has no obvious answer. But it should be apparent that cleverness is very desirable here.
You have a bunch of orphaned baby orcs. What do you do with them?
You've just gotten 1,000,000gp and your DM doesn't allow you to buy magic items. What do you do with your vast fortune? (I'll admit that this can turn into a question of "what's coolest?" for some parties, but for parties that are sincerely dedicated to making the campaign world a better place, it's a question of "how to best improve this campaign world with a million gold?" and that is much more interesting.)
Although I've presented all of these dilemmas as binary or limited multiple choice, the truth is that players are free to try all sorts of wacky things. There's no limit to what players are free to try (even though there is a limit to what has a reasonable chance of success).
And so I've avoided listing outside-the-box options for simplicity's sake. Not because they don't exist, but because they are usually riskier and/or more circumstantial.
Desirability of Dilemmas
Now that you've read a million words about dilemmas and are excited to insert them into your next session, I want to talk about why you shouldn't.
I think that, on average, DMs enjoy dilemmas more than players. We want to concoct big, dramatic decision points, and dilemmas certainly fulfill that role. But players often thrive on the small, discrete, and organic interactions that arise through play, like mushrooms on top of a mulch made of dead goblins.
Second, lots of players don't enjoy dilemmas. Perhaps they are here for beer, pretzels, and kicking down doors. Maybe they're completionists, and don't like their inability to solve all of the problems of all of the NPCs all of the way? Maybe they're pure escapists, and don't want any failures on their character's history (even if that small failure is accompanied by a bigger triumph).
Third, once you answered some of these questions ("yes, it is better for one to die so that three may live") they're a lot less exciting the second time around. Players usually player characters with nearly identical morals to their own, even when all other aspects of the character are very different from the player. It's easy to play a character that lies on the opposite end of the fashionista--slob spectrum from yourself; it's difficult (and sort of un-fun?) to play a character that you feel is doing the wrong thing, morally.
This is because you can't help but empathize with your character. If you are a Democrat, it's difficult to empathize with a Republican, even if that Republican is you.
Fourth and last, a lot of these dilemmas interfere with that particular brand of heroism that demands triumph over all evils, without concession. This brand of total heroism states that players can open the coffin and defeat the vampire within. They don't have to lick any boots because they can kick the balor's ass. They don't have to choose between A and B because they can have both, and some of C as well. I've definitely met players that entered the game with that assumption. [Edit: I previously referred to total heroism as the "rule of cool" and was criticized for it. Rightfully, because it was a misrepresentation of the rule of cool.]
Dilemmas include sacrifices, sometimes trivial but sometimes painful ones, and that's not fun for everyone.
I'm actually hoping for some feedback on this post, so if you were hesitating about commenting, don't.