Text and Trails

Warning: This post requires some knowledge of Dungeons and Dragons roleplaying to understand its myriad references.

I can’t remember the exact year. Probably 1993. I do remember the basements, however. Plural. We were forced into multiple dark corners for this particular hobby, it being the time when some parents still worried that we were enacting satanic rituals. These were the places where epic fantasy came alive and we got to star in it. It probably goes without saying that we were all fantasy nerds back then. In those days it was a steady diet of J.R.R. Tolkien, Stephen R. Donaldson, Tad Williams, David Eddings, and Robert Jordan. George R. R. Martin came along for us a little later. I distinctly remember trying to hide a copy of Game of Thrones under my jacket in the high school hallway so my junior prom date wouldn’t see it in passing as she walked past my locker. Lord, I wish I could tell 17 year old me that in 20 years it would be the coolest damn thing around.

Dungeons and Dragons roleplaying brought the epic fantasy we read to life. Several of us dabbled in creative writing and being DM (Dungeon Master — the story architect and rules tsar who runs the game for their friends, a role that is both inspired and confrontational) but in those days it was our buddy Brian who had the mind to make it all work. We still remember those early player characters fondly. Heck, Brian revived them as ancient heroes in a current campaign he has run for over five years. I can say that the wild mage I played then, who had a penchant for using a Wand of Wonder to create elephants out of thin air ten feet above adversaries, still rankles him as a rule loop hole. (You should never have given me that wand, Brian.)

Part of the fun back then was that there were a couple rule books and maybe an adventure setting guide or two to build off of, that’s it. No internet to search and double check rule debates. No Reddit to get lost in the weeds. No Twitter to directly ask the game developer what they had in mind for a certain spell. We were left with our imaginations and the need to argue out any rule differences ourselves. 60 foot Fireballs and katanas that could attack six-times a round were a memorable result. As for those books, it turned out acquiring them was an adventure itself. In a memorable moment, Brian and I fell $1 short (taxes!) when buying our first Player’s Handbook and resorted to begging strangers for a buck in the mall. It worked, though I remember the benevolent donor following us back to Waldenbooks to make sure we really did intend to spend it on a book. (You can say we made our Persuasion check.)

Fast forward 20 years to 2015. The old crew was now in our mid-thirties. We had outgrown Dungeons and Dragons around the time Bill Clinton was reelected. But a new, fifth edition of D&D had just been developed and released by Wizards of the Coast. Fantasy, thanks to Hollywood, was cool in a mainstream way we had never seen before. All of a sudden, folks of our age cohort were playing again. Not just the nerds this time, either. Spouses, significant others of all stripes, and straight-laced acquaintances joined ad hoc groups of old school gamers. DMs were recruited or anointed. Recurring game nights became standard. And for those of you who don’t really comprehend what I’m talking about, this is a commitment. Most games last months if not years. Some are weekly game nights, others monthly or even less frequently — though usually hours long each time. All involve the unique backstory and particulars invented by the player of a character created who joins with others in a quest that sees them grow from a newbie adventurer to a world-conquering hero — or anti-hero, as murder hobos go. It is collective story telling and requires all the “authors” to do this together. The stakes are trivial and monumental at the same time. Characters face death; their players are often heartbroken to have to create a new one after calamity strikes the campaign.

I personally went from not playing in decades to 1) playing a Human Barbarian with a group of DC UL Backpackers and friends; 2) DMing a monthly wine-infused Friday night campaign with a few couples whose nerd men taught their ladies the roleplaying ropes (with Jay and Colin added to the mix for good measure); and 3) playing — I kid you not — a saucy female Halfling Pirate/Fighter in a weekly group of “Ambassadork” men with female player characters we nicknamed the Spicy Girls (Sergio put up with some crazy stuff from us as DM; and Marcus, god bless him, brought us into his lovely home each week to host these antics; and Gary, god bless his soul, played with us as one of the last joys of his life before passing unexpectedly).

Over the years other groups came and went, including a memorable crew of wife/work friends/backpacking friends/HS friend/and cousin who joined me on a year plus campaign using Roll20, an online platform, when I moved to Haiti. A group emerged in Haiti itself, appropriately nicknamed “Dungeons and Voodoo.” A later group, DMed by Jerome, even allowed me to recreate my childhood wild mage as a sorcerer in the last in-person crew I was part of . . .

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Which leads me to the crescendo of this story: roleplaying in 2020 and the COVID-19 era. What was already a mainstay in my life — and many others too according to the New York Times, the New Yorker, and the USA Today — exploded as a virtual game night in households worldwide. I’ve never played more in my life, almost exclusively on Roll20. We couldn’t go out so we made the best of staying in.

My friend Jay leads a gallant weekly crew through the vampire horrors of the Curse of Strahd. He even got us up to 9th level already. My original crew of high school friends has joined up for not one but two regular weekly sessions. On Friday nights the OG early 90s crew gets together, Pete – a sharp witted lawyer – DMing, to take on a pirate-themed quest set amidst the Ghosts of Saltmarsh while we talk about wives, kids, work, and whatnot, and another midweek game night, Pete also DMing, involving a few extras, like my wife Cheryl, Pete’s sister Josie, and Justin’s friend Andrew. In one notable week both crews unrelatedly decided to take on — and lose dramatically — to two different dragons. We now know not to mess with Pete’s dragons.

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Roleplaying is spontaneous. It’s challenging. It’s frustrating. It’s also acting and escapism. Most of all, it’s a great way to spend hours bonding with friends. What could be more necessary in 2020?

Hats off to the Fifth Edition of Dungeons and Dragons. None of this would have happened without a well-crafted and balanced set of rules and background to create vivid player characters set amidst fantastical worlds. And it wouldn’t have worked as well virtually without Roll20 (and Pete’s Zoom account). But it definitely wouldn’t even be possible in the first place without great friends with creative minds.