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How It All Started

A Pre-Pandemic Alpha

It was the winter of 2019 and I had just recently moved into my house in Arlington, MA. My wife and I barely squeaked into homeownership before the real estate market went insane as a result of a global pandemic. My childhood friends David and Jennifer (as well as her husband Dan) flew from Florida and California respectively for a vacation.

But not just any vacation: they would stay for five nights and we'd play Dungeons & Dragons in an attempt to complete a campaign I had written when I was in my teens, some twenty years ago.

Prep Will Be the Death of Me

Needless to say, we did not finish that campaign.

But we did play for about six hours each day, desperately trying to get there. Insanely, it took me three months of prep to prepare for those five nights, consulting the shelves of 2e source books at my disposal to create character sheets, NPC stat blocks, monsters, and maps, to gather countless reference images on Pinterest, to write and rewrite the 5-part adventure module that would comprise their characters' final adventures. Admittedly, it took so long because I wanted this experience to matter. Jennifer's husband Dan never played a roleplaying game before, so I wanted him to come away from it with something incredible to remember. After all, he was journeying across the country to spend six hours a day in a dimly lit room with two strangers and his wife in a frigid New England. It also took so long not just because I wasn't a good Dungeon Master and hadn't played Second Edition in almost ten years, but because the game itself requires a lot of work, due to the way it is constructed.

AD&D 2e is crunchy and sprawling and lacking in unified game mechanics, there's no way around that (although I'm sure diehard afictionados will debate this point). I never remembered D&D being so much work to prepare for, maybe because the last time I had done this sort of work, I was in my teens and had all the free time in the world. Back then, my eyes didn't glaze over looking at pages and pages of tables.

As an adult now, I don't have that time to waste.

People Make Adventures Interesting

Long story short, that five-night was a success.

But what I realized is that it wasn't a success because of all my prep. In fact, all that prep material somewhat handicapped my ability to get my players to a conclusion. On the eve of the final night, the three of them were deeply unsatisfied with where we might be ending the adventure—two chapters short of a real conclusion, in an empty tower stalked by a murderous mindflayer, that had been reduced to tedious dungeon crawl.

Jennifer and I decided we wouldn't let things end this way. We stayed up all night and rejiggered the final adventure. "People," Jennifer reminded me, "are what make adventures interesting." And she didn't just mean NPCs—she meant the players and their characters, too. For this whole ordeal to be satisfying, it had to mean something to the players, and more specifically, to their characters. Yet my tower was devoid of people. What Jennifer was pointing out was something I had believed all along, but had forgotten: that the reason why we were all so invested in the RPG was because we wanted our characters to fulfill their destinies: whatever those destinies were. That's why we played RPGs. Not to roll dice—and controversially, not to "find out what happens," either—but to play through those epic moments we envisioned for our characters when we first conceived of them.

As a result, the adventure ended very differently than I had originally imagined. Jennifer and I pulled all the narrative threads from the chapters we'd never get to and tied them to this episode as plausibly as possible. The tower became the tower belonging to the alchemist grandfather of the party's fighter (David), that they had been searching for all along. At its peak contained those secrets' the party's plucky apprentice (Jennifer) sought after. And I filled that tower with a band of thieves and a slimy guild master plucked from the backstory of the party's wizard (Dan), whose need for revenge against his former business partner exceeded his need for self-preservation. Hijinks and fireballs and swordfights ensued.

Not Just Playing to Find Out

We still played to find out what would happen, but what happened at the table mattered, in a very personal way, to all involved. And while Dan would later tell me that the content of this session would be an experience he would never forget, I still knew something was missing.

The rules, despite being great at simulating fireballs and swordfights, did not help at all when it came to facilitating the story beats necessary to get to the satisfying narrative conclusion we all fought so hard for.

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