As a game master, my favorite moments during session come when I sit idle as the players’ debate the tough choices open to their characters. Each option balances hope with a price. All the options lead to consequences that will spin the game in a different direction. Watching these discussions, I know the game world has come alive. No one tries to metagame what they’re supposed to do. Later, when those same players wonder what might have happened if they had chosen the other path, I bask in that moment.

If players just wanted to follow a story, they could have read a book. In role-playing games, much of the players’ fun comes from making choices and then experiencing the consequences as the game spins into a new direction. A hard choice lets players reveal their characters, reminds players that they control their characters’ fates, and turns the game world into a vibrant place that reacts and changes.

Occasionally tough choices spring naturally from the twists of your game, but you can plan your game to pose more dilemmas for players.

What makes a good dilemma?

Dilemmas have consequences

Much of the fun of making game choices comes from seeing the effects. If the adventurers get a call for help from a fishing town threatened by raiders, the hard choice comes when they learn of a far more lucrative job: The cunning Lady Redblade wants a magical curiosity retrieved before her rivals can snatch it. When the curiosity proves to be a dangerous artifact, the hard choice comes when the players must decide whether to hand it over. Every GM can tell such choices matter, but the consequences must ripple into the game. If the players spurn the town, it burns (even if you prepared for a rescue session). If the players betray Lady Redblade, she treats them as enemies (even if your plot assumed she would remain an ally). If players seldom see their actions lead to repercussions, they learn that their actions hardly matter.

Still, consequences don’t make a good game. If you put a dracolich behind door number 1 and a pile of +5 swords behind door 2, you just offered a choice with consequences. But your players will still drop out of your crummy game.

Dilemmas require information

If you play Dungeons & Dragons long enough, you hear of a Monty Haul dungeon master who loads treasure on players. The name comes from the Monty Hall, host of a game show called Let’s Make a Deal. He handed out so much treasure that every bumblebee and Raggedy Ann left his studio with a vorpal sword. Sometimes, Monty offered contestants a choice of whatever lay behind three doors that concealed prizes ranging from a toilet plunger to a Chrysler Cordoba. Guess a door makes a dull decision, but Monty’s game entertained by creating dilemmas.

After a contestant picked door 1, but before revealing its prize, Monty would pull out wad of cash and count off bills that he offered in exchange for the unseen prize. Now players faced a dilemma.

Interesting choices start with information.

If the players must decide whether to travel the low road or the high road, the choice only merits a coin flip. But suppose on the low road, the hag Auntie Boil always demands some small, wicked deed of those who travel her swamp. On the high road, frost giants guard an icy pass, but one may owe the thief a favor. Now the choice becomes interesting. Players can expect their choice to take the adventure on a different spin.

Menus of choices like these let players reveal their characters or steer the game toward their own preferences. I like offering such options near the end of each game session so I can prepare for the road ahead.

Dilemmas defy correct answers

Sorry Monty, but choices with one right answer don’t count as dilemmas.

Such choices might serve as puzzles. Suppose the PCs want to pursue the Dread Baron, but wonder whether to follow the low road or the high road. If they see he left his fur boots in his tower or if they find an invitation from Auntie Boil tied to a bird in the rookery, then they know which road to take.

Puzzles like this enhance your game, especially if you occasionally allow the players to miss the clues. Virtually every adventure spins clues and other leads into the threads that draw players along. But such clear answers only offer a choice between continuing the adventure or dropping out. If players know which road to take, they gain no sense of freedom.

In a dilemma, every option brings a price

In the choice between the high road and the low road, each option brings a price: The high road means calling a giant’s dept and hoping a he will honor it; the low road requires some wicked deed.

“To craft a good dilemma,” Wolfgang Baur advises, “Don’t give the players any good options.” (See “Dungeoncraft – Temptations and Dilemmas” in Dungeon issue 148.)

Clever players may still find good options—players relish the chance to crack an unsolvable problem, but you don’t need to hand them a solution. And definitely don’t hand them a fight. Usually, a good dilemma puts PCs between forces too strong for an assault. If you make Auntie Boil or those giants look like a problem that just needs a few smacks with a warhammer, you created skirmish rather than a dilemma.

Creating dilemmas

The limits of loyalty and time can easily create dilemmas for players.

As player characters gain in renown, powerful non-player characters will begin to request or demand their loyalty. If Lady Redblade and the Master of Eyes both want the players to retrieve the same magical curiosity, then the players choose more than an ally—they choose an enemy.

The limit of time can create many torturous dilemmas. The players must understand that accepting Lady Redblade’s job means risking that besieged town.

We DMs tend to offer quests with no particular urgency. This spares us from having to rework a mission because the game world moved on. The fishing town perpetually waits on the verge of doom until the players arrive to save it.

Sometimes though, time must force the players to choose which fires to fight. This does more than test the players. Such dilemmas make the game world seem like a dynamic place that moves and changes even when the PCs turn away.

Let’s Make a Deal

Suppose you know that the paladin in the party would never spurn the townsfolk for Lady Redblade’s bounty. Now you can play Let’s Make a Deal. The heart of Monty’s game came when he started counting off the hundred-dollar bills that he would exchange for whatever prize lay behind door number 3.

For the paladin’s help, the Lady can offer that magic sword he covets. “So armed, imagine the good you could do.” If she offers to send her own men to aid the town, will the party take her job? After closing a deal, what happens when the party learns that the man assigned to rescue the town is corrupt and possibly incompetent? Do you betray the Lady and your word, or do your leave the townsfolk to their uncertain fate?

Let players feel powerful sometimes

Don’t turn every decision into test of the characters’ limits. A few tough choices add to the game, but people also play to feel powerful enough to sweep away trouble with an stroke of the blade and a fireball. Read the mood of your players.

Still, even if you work to put players in dilemmas, hard choices can be hard to create. That’s what makes them so delicious.

Related: Strong Moral Dilemmas in D&D and the Unwanted Kind that Keeps Appearing
Dungeons Masters Can Make Fake Choices for Players, But Should You?