Fighting Dragons In The Mind: My Relationship with D&D

I owe a lot to Dungeons and Dragons

For the uninitiated, Dungeons and Dragons (D&D) is a role-playing game. Each player at the table takes on the role of a character, usually representing some combination of classic fantasy archetype such as Elves, Thieves, Wizards, Skeleton Pirates, Hippopotamus-Men, etc. They control everything that character does. One player, the Dungeon Master (DM), is in charge of most of the storyline and controls all of the non-player characters and monsters. The game itself is very free-form and flexible. If you think your character could do it, you can try it. Goblins terrorizing a village? You can try to kill them or hire them to attack someone else. You can adopt them all and be proud Goblin-parents, or pretend to be their Goblin-God and get them to do your bidding. The game is governed by dice to determine if a character is successful, with certain rules outlining what types of characters excel at certain activities. Combat, social situations, and complex tasks can all be determined through dice-rolling.

The thing that sets role-playing games like D&D apart from other games is that there isn’t a set victory condition. The story keeps going until the players all decide it’s over. The characters can set their own goals, choosing how they want to make-believe their way into or out of any situation. At the end of the day, it’s little more than sitting at a table and fighting Dragons in your mind. At its best, D&D involves a group of people creating a collaborative experience full of tense moments, using the rules as only a guideline to drive the story. It’s a board game with no winner, a writing exercise with more constraints, and a great way to spend an evening.

Comics & Chimeras

In late 2006 my cousin Jacob and the rest of his family were in town for the Holidays. Our hanging out mostly consisted of taking turns watching each other playing single-player games. Jacob is a year older than me, and I always looked up to him as someone with great taste and knowledge of fantasy, sci-fi, and gaming. It was at this time that I saw Jacob reading a D&D-based webcomic, The Order of the Stick. Back then they were on comic strip #400. At the time of writing this, they now have over 1100. I started reading the comic from the beginning.

Art Credit: Rich Burlew

The Order of the Stick is a fantasy comedy comic, in which all of the main cast are D&D characters in-universe. The comic differs from most D&D webcomics in that the characters never reference having players, or even the existence of a DM controlling the story. It’s a comic set in a world that happens to be governed by the laws of D&D. For the characters, the existence of the sky above them is as true as the existence of attack rolls and skill points.

My only knowledge of D&D at this point was the stereotypes I had picked up from shows like Dexter’s Lab or Recess. There was an entire episode of Recess devoted to “The Pale Kids”, a group of reclusive 5th-graders who’d rather stay inside at recess in order to play a game that totally completely definitely wasn’t D&D. They had weird in-jokes, dressed funny, and had little social skills. Despite all these stereotypes, which ranged from true to sadly true, I dove headfirst into acquiring as much D&D knowledge as I could. I scoured the forums for every mention of D&D I could. I knew tons about it before having ever rolled my first die.

In what was probably the summer of 2007, several months after I discovered The Order of the Stick and armed with all of the D&D knowledge I could muster, I finally had a chance to actually play the game I was so captivated with.

Museums & Manticores

The ROM has a summer camp, where kids age 5-16 sign up for groups to get to see the Museum with special instructors, learn themed lessons, and do arts and crafts or other projects. One of the groups for the older campers was Dungeons & Dragons. During the morning you learned about Medieval Europe, Feudal Japan, etc. During the afternoon, you got to play Dungeons and Dragons with your fellow 11-14-year olds and with one of the older staff members taking on the role of DM. The ROM’s D&D program started in the late 80s or early 90s, meaning that at this point it’s almost three decades old. My first DM was one of the staff members named Daniel, who has since taken over the program.

My First Character: Syvaris Snaketongue – Halfling Rogue

If I wasn’t hooked before, I certainly was now. The D&D program ran for two weeks at a time, and I got my parents to sign me up twice during that summer and multiple times in the next. Back then most of the D&D program’s educational content didn’t change much from session to session, but I gladly sat through the same facts about swords and armour in order to get to play the game. I took almost every opportunity I could to enrol in the program. I was now not just a camper, but one of the “D&D kids”. The D&D kids had a reputation. We never wanted to go outside during our lunches, and if we did we just sat around and talked about D&D. We carried stacks of strange books around the museum with them. Being the nerdy preteens they were, we also brought with us an intense body odour that had come to affectionately be called “The Fog of Eternal Stench”. We were an odd bunch, in that we paid money to spend our summers in a museum fighting Dragons in our minds.

Once I turned 15, I was officially too old to sign up for the D&D program any more. I tried running the game myself for my friends from school, but it never really took. When we hung out we were just as likely to get distracted and play video games instead, and there was never any semblance of continuity. We had fun, but it was never quite the same as the D&D program.


First Online Game  Character: Durx Ironbeard – Half-Orc Cleric of St. Cuthbert

Having outgrown the ROM’s D&D program, I did the next best thing I could. In high school I became a Summer Club volunteer. I saw getting to volunteer for the D&D program as the highest honour, and made that my goal. I went through my whole first summer volunteering in other groups, helping kids learn science and make pottery, but was never assigned to the D&D program itself. They usually liked to have the older staff members with the older campers.


Undeterred, I worked at the ROM for a total of two summers, two march breaks, and almost every Saturday morning during two school-years. I was able to land a position for my last March Break of high school. I had made it to the big leagues. Honestly, it’s safe to say that I peaked, and the rest of my life will just be the (hopefully) slow descent down from this nirvana. You see, during that March Break I was paid to help 12-year-olds fight Dragons with their minds.

Growth & Gorgons

D&D itself was important to me, but the game also introduced me to other things that have been really important for me as well.

D&D at the ROM was crucial to me for other reasons. In middle school I usually only talked to my small group of friends, and my High School itself was tiny. For a sense of perspective, my graduating class consisted of a twelve people, and the school itself had only forty-six students. During both my time as a camper and as a volunteer at the ROM, it was an important social outlet for me. I loved my school to death, but I wasn’t getting a representative experience of what people were like from that small sample of people I talked to every day. Crucially, you could never have a falling-out with someone at my school, as you couldn’t help but run into them and have to see them daily. Similarly, you practically had to be friends with everyone in the school. It wasn’t really until the ROM that I realized how I treated people could have lasting consequences; nothing was forcing you two to be around one another, so I had to learn how to not be a little shit. They wouldn’t give me a second chance, and they didn’t have to forgive me. Sometimes I had to learn this the hard way.

D&D also set the foundation for my interest in improv. Role-playing was my first foray into acting, and through the D&D forums I was first exposed to collaborative storytelling. Sitting around with your friends, making up stories is basically improv with a table. I realize that a lot of my comedic sensibility originally came from Order of the Stick. I wouldn’t try doing improv myself until university, but D&D certainly sowed the seeds. Eight years after I started playing D&D and one year after starting improv, I met my girlfriend Kristen through McMaster’s Improv Team. I tried playing D&D with her early into the relationship, and she accidentally named her character Maggie Smith and got frustrated with dice rolling. In improv whenever you do something it just works without fail. She vowed to never play D&D again.

After a lot of prodding, it only took another four years to convert her to a regular player of the game. Now we both can’t shut up about it.


Most Recently Played: Orindi Griemhild – Air Genasi Monk

Because of D&D I also became a digital artist. I always loved drawing or doodling, but my time on The Order of the Sticks’ forums was instrumental in getting me to draw through a computer. I joined a thread called “Avatar Battle Royale”, where players would draw their forum avatars fighting other users’. Drawing your characters punching, slashing, or exploding one another eventually evolved to storylines, plot, and continuity with dozens of contributors totally thousands of instalments. Taking part in online D&D games required applying with a character, and I found that you were more likely to get in if you had custom artwork. I tried starting my own webcomic, twice. I drew other people’s characters and forum avatars for them. I’d come home every day from school and spend two or three hours every day drawing. To this day, the style that I use to draw characters is one that evolved from the same style of The Order of the Stick. Sadly, most of the stuff I’ve made has now been lost to the void, as the file-sharing site all my stuff was hosted on,, went under. On the one hand this is great, because I now have no record of my shitty MS Paint drawings I started with. On the other hand, that means you guys don’t get to see my shitty MS Paint D&D drawings.

D&D has been vital for my mental health, in a roundabout way. The game itself often served as a distraction from crappy situations. When I went through my first breakup, the first people who I felt comfortable talking about it with were the online friends I had made through the forums. Going from living at home and going to a school of under fifty students to living alone in a school with tens of thousands meant that I had a really rocky transition. I wasn’t the best person back then, and I treated a lot of people in really regrettable ways. I can’t even imagine how much worse I would have been had I not been exposed to people through the ROM. I went through an incredibly tough first year, and improv practice was sometimes the only thing that would get me out of bed on a given day. Were it not for D&D, I wouldn’t have had the tools I needed to get me to where I am today. Sometimes we all can feel like we’re fighting Dragons in your mind. Fighting pretend Dragons let me be able to fight the slightly-less-pretend Dragons that came into my life.

Present Day & Purple Worms

In my undergrad I stopped playing D&D. I didn’t enjoy playing with the “Nerd Club”, who ran weekly events, and they often conflicted with improv practice. I tried a handful of times to start running games, but they quickly fell through because of time commitments and scheduling issues. I probably tried to start a half-dozen games or so, but they almost never lasted more than one session. Just like in middle school I wasn’t great at getting a given game of D&D to keep going unless it was part of the ROM’s D&D program. For  about five years, D&D was almost gone from my life.

The summer after my final year of undergrad, the incoming co-president of Mac’s Improv Team hosted a cottage weekend. After last year’s camping had been nearly rained out, hanging out with a roof over our heads and with tables became incredibly appealing. One of the members of the team, my friend Matt, brought D&D. There were over a dozen of us, split into two different groups, with only Matt and I having any longstanding experience with the game. I helped people make their characters, telling people what their characters could do and giving them rules advice. I hadn’t really played D&D for years, and most of my time had been spent DMing for other groups. On that Saturday night we started playing, and it all came back to me.

I was back in.

As soon as I got settled back in Toronto, starting my Master’s degree, I knew that I wanted to run D&D again. That summer I ran a game online for strangers; I couldn’t wait for September to roll around. Toward the beginning of the first semester, I put out the call to whoever would like to play. I received tons of replies. Friends and acquaintances from Mac, high school friends I hadn’t seen in years, new classmates in my grad school, fellow ROM staff, new friends from improv class, my sister’s boyfriend. I couldn’t take everyone, and scheduling is always a thing, but I’m happy to say that the eclectic group we put together has been playing the game almost weekly for nine months now. Most of these players haven’t played before, and I get to share time and the game I love with a new generation of players. In the months since, the players have since forcefully imposed democracy on a town that didn’t want it, adopted and subsequently accidentally murdered an evil puppet, and made a batch of poisoned scones “just in case you need a poison scone”. You know, hero stuff.

My Current Players: Adelia Newtspew, Felix Oswald Gearhart, Gravy Scones, Sloane Bloodhammer, Mack Barrow, Mahkah Anthu, and Nat’

So what do I owe to D&D? Where it not for D&D, I wouldn’t have had my volunteer hours, improv career, first job, interest in board games art skills, my girlfriend, most of my other friends, or a sense of personal accountability. Not bad for coordinated make-believe.

If you ever want to be a part of this amazing game, but you never knew anyone who played or found it intimidating, let me know and I’ll help you out. It’s never too late to start fighting Dragons in your mind.

JULY 18 UPDATE: Want to make your first character? Here‘s a guide I wrote on it!

2 thoughts on “Fighting Dragons In The Mind: My Relationship with D&D

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s