We as GMs and DMs are always on the hunt for that perfect story idea, that shocking twist, that ideal NPC to provide the game we want. You can find or engineer those things--I've addressed campaign ideas twice before as well as how to make lovable allies and interesting villains (plus a list of villains to use). Other things feel more elusive. How do you ensure your players will engage with the story? How do you give them room to roleplay and define the story? How do you push them to play based on ideas rather than strategy? Fortunately, I have a way to accomplish all three of these things: philosophical conundrums. A good philosophical conundrum makes the players use their brains, which means trying to think as their characters. As I'll describe below, that's one of the most rewarding things we can introduce as GMs.
What exactly is a philosophical conundrum? In essence, it's an issue of some sort that's difficult to resolve (conundrum) due to the philosophical implications of the issue itself. A classic example of this idea is called the Ship of Theseus. The story goes that the Ship of Theseus goes off to sea, and over years of damage from battle and the elements, many parts of the ship have been replaced. In fact, the whole ship has been replaced at one point or another. The question is, is it still the Ship of Theseus? Do the changes make it something new, or is it just revision of a constant whole? This philosophical conundrum is more an intellectual exercise than what we want as GMs--we want something practical that requires action--but it illustrates the concept. What we really want is some issue that enters moral territory.
In order to really engage the players, we want an issue that is complicated and messy. This will get a direct and real reaction from the players, for one, and for two, it makes your story more engaging by having a connection to the player's own values. The standard construction for this type of story is that someone is doing something, and that something is both really good in outcomes for some people and really bad in outcomes for other people. By way of more concrete example, new settlers in an in-game territory have helped improve the lives of the people already living there, but this new relationship is threatening the culture of the people already living there. Some will argue that the livelihood of everyone is the most important issue, and others will argue that the culture is too important to lose. As the players move through this story, you can continue to layer in details that further complicate the scenario. In the end, you'll have a complex moral issue that the players will have to resolve. (And they'll love it.)
I promised that philosophical conundrums give us our best chance at three important things: engagement with the story, providing space and inspiration for roleplaying, and making them think inside of the game. Let's address how using examples of campaigns I've run that have included philosophical conundrums and how it's gone.
About two years ago, I ran a mystery campaign for a group of friends I've been playing with for years. You can read summary and analysis of the whole campaign, but in brief, the party was tasked with solving a murder; in their pursuit, they were required to gather clues and witness testimony to discover the killer. As they worked, they discovered that the richest person in town, a known philanthropist, was somehow involved. I'll leave the rest for you to read if you choose, but the philanthropist detail was a big complication for the party. They encountered the philanthropist several times in the story and always had a difficult-to-articulate dislike of her, but it was only when she was implicated in the crime that that feeling entered the storyline. The idea of going after the benefactor of the city complicated the situation, and it caused them to pursue multiple other angles before going after her.
This is to say that the players were more engaged with the story than just solving a mystery would have prompted. Before I introduced the philanthropist to the story, it was a fairly procedural investigation; adding her shook things up and made the party take note of the larger city around them. But when she was implicated, the philosophical issue entered the fray. Now, their investigation would impact the entire city. It ratcheted up the tension, and it resulted in a series of serious discussions about what to do which hadn't happened earlier in the campaign. I spoke about this campaign with a friend who played in it recently, and he told me that his favorite part of the campaign was [spoiler redacted], which entirely relied on the reveal that the philanthropist was involved in the murder. It really was the moment that placed the campaign on the final stretch, and I'm really glad I could pull them in with this simple philosophical conundrum.
Why does this work? Well, I think of it this way: there are practically limitless ways to play tabletop RPGs, all of which engage the brain of a player differently. A combat scene makes the player think strategically and according to structured rules. A puzzle scene requires logical thinking and caution. A roleplaying scene involves abstract thinking and imagination. Good battles and puzzles engage those ordered thoughts, but for roleplaying, a good story asks the players to take a personal stake in the action. It's not "we have to win this battle to keep playing the campaign"--it's "we have to win this battle because hundreds of people will suffer if we fail." Having played in both kinds of situations before, I can tell you it feels completely different to be totally engaged with the story. And philosophical conundrums make us engage deeply because they bring us further into the story and world.
Much more than two years ago, I ran one of the first D&D podcasts ever. Our show, called Listen Check, was a showcase for roleplaying. With an audio only medium, relying on roleplaying seemed a logical choice, which was nice because it was already what we wanted to do. The first quest they encountered in our three-year campaign was a conundrum: the orcish god Gruumsh wanted the party to help him get revenge on the descendants of people who had slaughtered orcs in the past. This presented a philosophical conundrum in that not righting the wrong was morally upsetting, but carrying out Gruumsh's wrath on people who didn't commit the crime. Further, Gruumsh was demanding the deaths of the governor and sheriff of town, and this only complicated things. The party was always in support of turning against Gruumsh, but they often wavered--frequently, they would discuss alternatives and revisit old conversations rather than commit to one position completely. And because they were always debating this issue, there was a great opportunity for roleplaying.
An opportunity for roleplaying really depends on your campaign, but if you're focusing on roleplaying, it's priceless. And the truth is that the most reliable source of material for roleplaying is a discussion of what all the players are going through together. And beyond that, what they're going through together is the story of the campaign. So if there's some complicated issue at the heart of that campaign, there's essentially endless opportunities to roleplay. In the campaign I'm in now as a player, our DM has us acting as diplomats to the hostile elven government, fighting for peace. Just about every time we have downtime as a group, our complicated main quest comes up. I often wonder in character how my quiet con artist (who used to pose as a diplomat) ended up part of a royal diplomatic party. It's a rich source of roleplaying for all of us, and it's only apparent when the GM makes room for it. A good philosophical conundrum can do that for you.
Why does this work? Well, I think of it this way: most of us don't create literally multiple novels of backstory for our characters, so we need some reference point to respond to. And having something to respond to means that the GM or another player needs to give input. Most of what a player says is more roleplaying responding to other players roleplaying, but GM input can go beyond that moment. GMs know that typically, any sufficiently interesting detail will be discussed, but this is usually for only a moment or two. A philosophical conundrum gets greater distance because the details you add to complicate the conundrum change it enough to inspire new discussion. I remember that on Listen Check, revealing that an arch-villain they players fought in the middle of the campaign was actually a possessed but sweet-hearted and helpful NPC from a campaign I'd run with mostly the same group of players. This detail--the NPC's backstory being cherished--made fighting him harder, and the players were even inspired to try to save the character after defeating him. That kind of roleplaying doesn't happen when you're just fighting goblins.
The last element to consider is making the players think inside the game, which philosophical conundrums accomplish perfectly. To provide an example, the first real campaign I ran (ever more years ago now) involved an ill-conceived story about the party infiltrating the city guard and assassinating all the important governmental officials. The party abandoned it almost immediately, turning on the questgiver, who revealed themself to be an avowed anarchist member of the royal family, seeking to destroy her family's kingdom. The conundrum was that the kingdom was doing a generally good job (no civil unrest), but the anarchist had stories about terrible corruption. The result was the most dramatic response to a philosophical conundrum I have ever seen: the party split in half. Half of them sought to topple the kingdom, and the other half strove to defend it. The campaign ended in a climactic battle, a draw. We ended the campaign with a fractured party, and everyone couldn't have been happier.
The thing that went completely right with this situation was that the players did something really special: they thought inside the game. It would have been easy to say, "We don't want a party split--let's just agree to defend the kingdom" and go on with the mission. But they decidedly didn't do that. They thought as their characters, and it transformed my bad writing into a really exciting story. Watching the players work against each other in front of each other became one of the thrills of that campaign. Seeing how different situations arose and unfolded was exhilarating. It was all a product of how the conundrum made the players think. Once they were thinking as their characters, it became suddenly possible to give them further and further prompts to define the story. In one climactic moment, the head of the anarchists assassinated the king, and the defenders brought in a cleric to revive the king, leading to a series of complicated rulings on my part that led to the final battle. This again shows the great value of a conundrum--the players weren't just fighting to win the conflict against the other players; they were fighting to do what they believed was right.
Why does this work? I think of it this way: it's a sink-or-swim roleplaying prompt. At the end of the day, roleplaying really just comes down to thinking as your character. And a philosophical conundrum demands one of three responses: you simply don't know how to respond, so you guess (sinking); you consider the conundrum from your own perspective as a human being in reality (sinking that looks like swimming); or you think about what your character would think (swimming). The good news is, almost nobody completely sinks. Answering for yourself instead of your character is unfortunate but can't be helped--you can't make someone roleplay. But you can give them an incentive to. And a philosophical conundrum is a great incentive. I'll tell you now that I have GMed for dozens and dozens of people with no interest in or history of roleplaying, but if you offer them a philosophical conundrum, I'd say 90% of people will immediately catch on. I've GMed for large groups of sixth graders before, and even most of them get the prompt. A philosophical conundrum makes you use your brain; encountering a conundrum as your character makes you feel inclined to use their brain.
So there you have it: a variety of ways to think about conundrums and their role in your games. As a bit of a post-script, I want to mention a tabletop game that I've created (but not published yet) that uses time travel. (You can play a short time loop adventure I wrote here in the meantime.) The larger game basically uses a mechanic that changes the rest of the timelines you can visit based on your actions. And as players make changes, and as intentional and unintentional side effects pile up, it inherently creates philosophical conundrums for the players to deal with. As you can see, I'm very passionate about these conundrums, and I hope that experimenting with them in your games shows you why.
That's all for now. Coming soon: home décor by culture in my homebrew setting, lessons from GMing for children, and how to know what class to play. Until next time, happy gaming!
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