How Do I Win? | Andrew Gu

“What’s the goal of the game? How do I win?”

Those are the two most common questions I get from new Dungeons and Dragons (D&D) players, and just like the question “What do you do in Humanities Conservatory?”, the answer is a little complicated.

For many athletes, winning is clear-cut, usually involving getting more points than one’s competitors (golf doesn’t exist). For video gamers, winning might mean beating all of one’s enemies, solving all of the puzzles, getting past every obstacle, or checking every task off of a mischievous goose’s list. For readers and TV and movie watchers, it might just mean getting to the end of the story and enjoying the ride along the way.

For D&D players, winning might be all of those things or none of them. The rules of D&D, unlike those of a sport or video game, are more suggestions than anything else, providing a structure for smoothly running a story more than hard-and-fast restrictions. As a tabletop roleplaying game, almost all of the qualitative imagery takes place in the players’ and the Game Master’s (the person tasked with creating the world and the story the players engage with) imaginations. That mix of rule-bending and imagination means that “winning,” much like winning in real life, is a nebulous, subjective concept defined by the participants; as a player, you might be “winning” if you’ve achieved a satisfying resolution to your character’s arc or if you’ve managed to get out a deadly ambush with two spells, a jug of oil, and a piece of string.

As a Game Master, I’ve struggled with encouraging new players to think of their own win conditions; our lives are so defined by external motivations, be they grades or bells or college applications or deadlines, that just figuring out what your imaginary character wants, let alone what you want to get out of an experience, can be bewildering.

But that bewilderment is part of what makes D&D so beautiful, so freeing. Our lives aren’t just checklists of externally-assigned tasks to complete; at a certain point, we decide for ourselves what “winning” means, and D&D brings that decision to the forefront. Like in creative writing, character motivations are everything; without them, D&D sessions are just thumping from task to task like a pinball machine, but unlike with creative writing, the players’ motivations also take center stage.

Even more so than video games, D&D is interactive. It’s not a group of players going through one story, it’s a group of storytellers with a reciprocal engagement with their world who organically construct their own stories in a way that no video game, no novel, no movie can replicate. The Game Master might present the players with a small town, for example, but it’s entirely up to each player to determine for themself whether or not that town becomes a piggy bank to break, a home base, or the start of some shenanigans the Game Master could never have predicted.

This isn’t to say that you need to go out and play D&D if you want to ever experience an interactive story. Everyone’s busy, and there are plenty of other opportunities for similar experiences, as well as plenty of other tabletop roleplaying games. Of course, if you have time or interest, I highly suggest checking it out, but if you don’t, at least consider the meaning of winning. Is it when you’re satisfied? How do you know when you’re satisfied?

Those aren’t questions I, a seventeen year old nerd in an article about tabletop gaming, can satisfactorily answer, but they’re worth considering; otherwise, we all lose.