How the Mechanics of Tabletop Roleplay Games Can Get Writers Unstuck During the Drafting Process

This piece has been cross-posted from JessicaHatch.com/Blog.

I’ve been playing Dungeons & Dragons for a year and a half now.

I’d always been curious about D&D, but I grew up in the Southern Baptist church, which had these horrible things called Chick Tracts,* which warned our parents that this nerdy bit of fun was really a vehicle for summoning the devil. Long story short, I wasn’t allowed anywhere near it.

Now, as an adult, this game is a highlight of my biweekly schedule. The year and a half that I’ve been playing D&D is the same year and a half that saw my first two novels published and in which I was formally diagnosed as autistic. Unlike everyday life, which can be stressful, exhausting, and sometimes feel like everyone else got their lines ahead of time, D&D provides a safe space for kids of all ages to play make-believe. The fact that there are rules and risks taken for everything from who goes first in a fight to whether you can persuade a dragon not to fire-breathe you to smithereens appeals as much to my hyperorganized side as it does to the side that binges trashy reality TV.

So when I started figuring out a fresh project to work on this spring and summer,** the subject matter was a no-brainer. Drawing inspiration from the work of Helen Hoang, Travis Baldree, and Caden Armstrong, Roll for Initiative (working title) is a romantic-comedy-in-progress about Grace, a lonely bookseller who joins a D&D party around the same time that she gets her late-in-life autism diagnosis—and she may have some spicy dalliances along the way.

“Alea iacta est [the die is cast].” — Julius Caesar

I like to have my outline fleshed out before I start drafting, but with Jami Attenberg’s #Mini1000Words event going on earlier this month and the exposition jotted down, I thought I’d take a crack at Roll for Initiative’s opening chapters.

In chapter 2, Grace meets the other members of what will become her first ever D&D party when they blow through the bookshop where she works. I knew these puckish men and women needed to reach the point of inviting her to join their group, but I was supremely stuck on (a) how Grace would be charming enough for the party to invite her to join them and (b) how introverted Grace would respond to three strangers asking her to play a game she’d never played before (even if she found two of them attractive and incredibly charming).

Instead of forcing my brain to create a lackluster and possibly unconvincing beat sheet, I took my solution straight from the pages of the Player’s Handbook (Fifth Edition) and made all characters involved “roll for it.”

How I Did It

Step 1: I rolled my characters’ ability scores and modifiers.

In D&D, every character has six ability scores: strength, dexterity, constitution, intelligence, wisdom, and charisma. These abilities are the basis of what a character is able to do with and without ease, so if, say, a player wants to be a fighter who can easily pass athletics (strength) checks, they’re going to put their highest ability dice rolls in the strength category. That’s not to say they’ll never roll poorly, but their chances of failing a related ability check are lessened. (More on ability scores and modifiers here.)

Based on what I know of the characters I’m writing and their personality traits, I rolled four six-sided dice (4d6), dropped the lowest roll each time, and assigned the resulting numbers and their modifiers to my characters. For instance, the character Cass is a bon vivant, so I put her highest roll into the charisma ability, which is responsible for checks like persuasion and deception.

Step 2: I jotted down the beats the scene needed to hit that were giving me a hard time with outlining.

The D&D crew needed to see something in Grace that would make them not only want to hang out with her but to do so in a concentrated gaming format, where sessions are usually four or five hours long. Grace, meanwhile, needed to see something in these strangers that would make her feel safe and interested enough to want to see them again.

These are big asks—what you get if, like me, you write high-concept novels about, oh, say, planning a wedding without having a fiancé or trying to save your old apartment building by pretending you’re not getting divorced—so I wanted to see if roleplaying them like I would in a D&D session would lend me any inspiration.

Step 3: I set up ability checks for these beats, picking from a difficulty class (DC) of easy (5 or higher), medium (10 or higher), challenging (15 or higher), or extremely challenging (20 or higher). This meant my characters would have to roll an amount plus their ability modifiers that was higher than the DC.

Maybe Grace could be exceedingly charming, drawing them in from the jump? And would (or should?) Cass and her friend Tom be able to persuade Grace to join their game?

I set the DCs pretty high here, given how unrealistic the outcome would be, with Grace’s charm check having a DC of 15 and with Tom and Cass’s persuasion checks having an even higher DC of 20. To pass these checks, the calculation is # on the die + character’s ability modifier + other fancy stuff like proficiency bonuses.

Step 4: And then, using the iconic d20, I rolled!

Grace is an introvert with a pretty low charisma score, so it was something of a given that she’d fail her charm check. When she did, I had to problem-solve. I decided to give her a softball with an intelligence check: she would know a lot about the subject matter of a book they were looking for, allowing her to appeal to a shared interest. Her intelligence modifier is high, so she passed the DC 15 check easily.

How It Went

I enjoyed the improvisational work this exercise required me to do. Honestly I might do this for other high-stakes beats in the first draft so the novel’s choices feel fresh and new, not like choices I’d automatically make, which risk being lazy—too same-y and uninspired. (I’ll zhuzh these dice rolls, of course, when I revise the draft, if it makes narrative sense to do so.)

I also really liked the spontaneity of the exercise. One fun and unexpected phenomenon was that Cass, the bon vivant character with a high charisma score, absolutely whiffed it on her persuasion check, rolling a 7. That’s the fun here: If I were brainstorming this scene, knowing what I know about these characters, I’d say, “Oh, Cass is charming as hell; of course Grace is convinced to join them, even if she doesn’t show it,” and that would be that. Leaving it up to chance allows us to see different sides of our characters and the situations they find themselves in, thereby making them three-dimensional. It also gets us as writers out of our comfort zone and out of the muddy narrative ruts the wagon wheels of genre can drive us into.

Ways to Try This If You’re Not into D&D

If you want to try this drafting exercise but your mind was reeling at my brief explanation of rolling ability scores and ability checks, there are ways to add chance into your drafting process without owning a d20.

You might ask yourself a question like, “In this scene, does my character convince his wife that he was home all night?” and then roll a six-sided die, like you’d get in any board game, with 1 and 2 meaning yes, 3 and 4 meaning no, and 5 and 6 being some middle ground. You could also do this with a Magic 8-Ball (“Try again later, you night stalker, you!”).

Alternatively, you might consider the characters in the room. Rather than picking the obvious person to further the action, randomly pick from among the other characters to see how someone else might move the scene from point A to point B.

There are tons of ways this can go, but just have fun with it! The first draft, in my humble opinion, should be all about creative play. That way, you can surprise yourself and, in turn, surprise and delight your readers.

Footnotes

*If you want to get a kick out of evangelical thinking during the Satanic panic, google “Chick Tracts Dark Dungeons."

**I have another manuscript in a different genre I'm polishing and preparing to shop around to agents.