How I Botched My First Time Running a Dungeon and Dragons Game

Share this post!

Series: RPGaDay 2019
This post is part 1 of 31 in a series of posts for #RPGaDay2019. Click here to see the next post.

RPG A Day 2019

Today is August 1st, which means it’s also the first day of #RPGaDAY2019. Today’s prompt is FIRST, so I’m going to tell you the story of how I absolutely and completely failed in my first attempt to run a Dungeons and Dragons game.

My Introduction to Dungeons & Dragons

The year was 2001. My best friend bought a copy of the 3rd edition Player’s Handbook, Dungeon Master’s Guide, and Monster Manual. He brought them to school and showed them to me over lunch. I rolled my first d20 — solid orange, with black letters — between bites of that rectangular, greasy school pizza that was so common in school lunchrooms in the late 90s.

I didn’t even know that tabletop RPGs were a thing. The closest I’d ever come to them was looking through a worn-out copy of a 1984 Battletech wargame rulebook that my brother had given me from a box of random books he’d purchased when I was six. That book had cool pictures of awesome giant robots, and unfamiliar terms like “2d6” and “d12” that didn’t make sense to me, but still somehow stuck in my brain.

My friend had played a couple sessions of 2nd edition D&D, but no one else in our group of friends knew how to play, and even though he had a little more experience than the rest of us, my friend wasn’t interested in being a Dungeon Master.

Looking through the books, I was caught up by the concept that, as Dungeon Master, I could share my own unique stories with my friends. I had been inventing storylines for my Lego figures and G.I. Joes and toy knights for years. So I volunteered.

My friend suggested that I have them play one of the premade adventures, since I had no prior experience with the game. The Sunless Citadel, maybe. Or Forge of Fury.

But I didn’t want to tell someone else’s story — I wanted to tell mine. The chapters in the Dungeon Master’s Guide about creating your own world really caught my attention. I was fascinated by the idea of guiding my players through an epic story, something like The Lord of the Rings or one of the other wonderful fantasy epics I loved to read.

My First Prep Session

My friends and I decided to get together after school at the end of the week for our first session. That gave me about three days to prepare. I’d rush home from school, grab my notebooks, and sit at my desk writing for hours. I had a long elaborate backstory about my world, full of powerful entities and deep history.

But by Thursday, I hadn’t planned anything for my players to do. I’d created continental maps and written details about my fantasy cosmology and astronomy. I’d created a fantasy calendar, with named months and special holidays. I’d created a big bad evil guy, a reskinned Sauron ready to brutalize and oppress my fantasy world if my intrepid heroes could not stop him. But they were starting at level one, and I needed something they could do now.

I decided to start with a simple encounter — orc raiders attacking as the party traveled along a road. I didn’t think about where that road led, or how the party had met, or any of those details. I was sure this one encounter would take up the entirety of our game session. Two attacking orc archers and two with swords. For all my hours of work, that was the entirety of the content I’d prepared for my players to actually do.

I thought it was enough.

All the hype and expectation came crashing down, and I was left sitting on the other side of the DM screen with my heart pounding in my throat…

The Big Day

Finally, Friday afternoon came, and we all got together at my friend’s house. Everyone had already made their characters over lunch at school, so we were ready to jump into it. I cleared my throat and began with the paragraph of lead-in text I’d prepared about the BBEG and his intentions to rule the world. I described the party walking along the road and then — orcs attack!

It was over surprisingly quickly.

The players killed the first small bunch of orcs I’d sent them against in a couple rounds, and then I had no idea what to do. I didn’t have anywhere for the players to go or anything for them to do, and when I tried to think of something, anything, my mind just gave me static fog.

I absolutely froze up.

All the hype and expectation came crashing down, and I was left sitting on the other side of the DM screen with my heart pounding in my throat, sweating and nervous and upset that I hadn’t done better.

My friend who had played before was trying to prompt me, and our other friends were just looking at me expectantly. I felt my face getting hot, and my throat closing up and I was so mad at myself that I couldn’t come up with anything on the fly.

I wanted to. I wanted to just wing it and lead my players along this wonderful adventure, but my brain was just in total short-circuit mode. The harder I tried to think of something to follow up the orc battle, the harder it seemed to grasp any coherent thought at all, and the more frustrated I became at myself. Finally I just squeaked out an apology, told them that was all I had prepared, and asked them if we could stop.

It would be years before I realized that I’d had a panic attack at that table, because I felt I’d let down my friends. Anxiety is a bitch.

The entire session was over in about 15 minutes. I was upset and remorseful, and apologized to my friends for wasting their time over and over again. Thankfully, I had awesome friends. They assured me it was okay, and that they’d loved my descriptions of the combat scene. We ended up spending the rest of the evening playing Kessen and Dynasty Warriors 2 on my friend’s PS2 and having a great time.

Getting Back On the Horse

At school the next Monday, I asked my friends if they would let me try again.

They were willing to give me another shot.

I printed off a free adventure from the Wizards of the Coast website, The Burning Plague, and studied it extensively. The following Friday, we tried it again, this time with me following the published adventure. The game went so much more smoothly, and we all had a blast.

Instead of trying to craft my own campaign from the get-go, I used the wealth of free adventures published on WoTC’s website once we finished The Burning Plague, daisy-chaining them one after another. And slowly, I started changing elements. I replaced an NPC with one of my own creation, or redesigned an encounter. I started including scenes and places between the published adventures, and became more confident in my own creations and more comfortable with improv as a DM’s tool.

By the end of the school year, my sessions were almost 100% original content.


I’m always proud when I see a play report from a new DM saying their first session went off without a hitch. Mine didn’t. Yours might not. But here’s a secret: it doesn’t matter how your first session goes. What matters is how every subsequent session goes, and that every time you sit down with your dice and your notes, you learn something new and try to be just a little bit better.

I’ve been playing Dungeons and Dragons for almost 17 years now. I’m still learning new things to add to my toolbox. New tricks and lifehacks to make running the game easier, new systems to change the way things work. Players still surprise me with their innovation, and even when I think I’ve thought of every possible path leading from a given scenario, players will come up with something I haven’t anticipated.

I’ve had plenty of sessions now where the players went off course from my prepared adventure. That used to terrify me. These days, I just roll with it — I’ve practiced the skill of improvising at the table, and trust my imagination and my experience to help me create a great experience for my players.

Let's Chat!
How’d your first session go? Tell me about it in the comments.

Share this post!

Leave a Reply