My D&D Journey: From Player to DM in a Few Short Sessions

In late 2015, my wife Nan lobbied our friend Maddy’s fiancé Tyler to start a new Dungeons & Dragons campaign so that I would have a hobby. She later came to regret this after the hobby quickly took over all of my free time and mental energy. My transformation from non-gamer to fully-committed tiefling bard was swift and total.

Nan had been concerned that I didn’t have much in the way of hobbies to keep me occupied. I would experience bursts of creativity and interest in a topic that would temporarily consume much of my attention; this resulted in a collection of rough takes of songs I recorded in a makeshift studio in our laundry room, several incomplete NaNoWriMo attempts, a few terrible scripts for never-made short films, and a lot of time spent wanting to create but never feeling like I had the authority to do anything well.

Maddy and Tyler had been dating for at least a year at this point. Tyler had been playing D&D since he was pretty young, spending some time with each of the editions, and eventually writing and running his own campaigns. He had plenty of experience bringing new players into tabletop gaming, and he was interested in sharing his hobby with Maddy among others. Nan floated to Maddy the idea that D&D might be something that I would enjoy, and would Tyler be interested in playing with John?

I had not been aware of any of this, so I was somewhat surprised when Tyler reached out to say that he is starting a new campaign, and that I can download a blank character sheet and start filling it out, and here is a copy of the Player’s Handbook that I can borrow, etc. It wasn’t that I was being invited to play, but more that I was going to play, and these are the things that needed to happen first and so I had better get on it so as not to delay the rest of the group. The imperative nature of the information that Tyler provided to me made it much easier to get on board.

At the time, I was working as a general manager for a movie theatre where I was responsible for at least 70 souls who worked to keep the place running and profitable. The job consisted of so much constant performance (n.b. I viewed my role as much more of a cheerleader than a boss, which meant 90% of my responsibilities involved putting on a happy face to keep spirits up in the face of perpetual, soul-crushing adversity—“What do you mean the movie’s sold out?! Why don’t you have more people working!?” –All of my guests, 2015) that the possibility of submitting to someone else’s command of my immediate situation came as a welcome relief. All I had to do was follow Tyler’s directions and play a part in whatever he planned.

Or so I thought it would be, anyway. I think I had expected we would be participating in a fixed story, similar to how one might read an exciting novel or experience a JRPG. As it turned out, my party and I ended up generating our own story within the framework that Tyler had created, almost entirely as a result of poking along the edges of reality whenever it seemed appropriate, not unlike Roger Rabbit slipping out of handcuffs only when it was funny.

Playing Tyler’s game led me into other games run by my friend and party member Cori, and eventually to running two games of my own with new parties in a world of my creation. The time between my first D&D session as a player to the first game I ran as DM was about eight months. I don’t know how other people have gotten into D&D, but I want to chronicle my own experience, both for my own recollection and also so that future players or aspiring DMs can find some inspiration.

So get out your d20, dear reader, and roll initiative as I take you into my first encounter with Dungeons & Dragons!