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Origins of a Roleplayer

Updated: Jun 21, 2022

This week, we’re going to kick things off by talking about how I first got into Dungeons and Dragons – and how, before I tried it, I totally thought it was just a lame game for dorks.

I didn’t get into role-playing games until I was in college. Before then, honestly, D&D wasn’t something I thought very much of – I’d heard of it when I was growing up, of course, but only in a very general sense. It was the same way I’d heard of fixed mortgages or vegemite or Pearl Jam; I knew it was a thing that people played, and knew next to nothing about it.

I had only two exposures to D&D before I became a player: The first was in middle school, when I went to summer camp, and my roommate and a few of his friends played during their free time. I would wander past their games and simply shake my head at them for obviously being so antisocial (before going off on my own to read a book or something by myself, while they continued to play a game with their friends – the irony was lost at me until many years later).

The second was early in my freshman year of college, when another student (who looked sort of like a red-headed Peter Jackson) walked up to me at a meet-and-greet event for new students, and asked if I played any games – he said I looked like I might be a fellow gamer. I told him I’m not much of a video game fan (which was also more true at the time than it is now), and he clarified he meant role-playing games. I shook my head and shrugged, and he walked away to look for more players.

I saw that kid around the campus a few times that year, and always thought he was a bit weird, but looking back now I’ve gotta give him credit for two things: One, he was bold – he walked up to someone he didn’t even know, and just approached them and asked if they were a fellow player. That’s something that takes a lot of courage (something I have only begun to appreciate upon reflecting on that guy in the past few years).

Two: That guy was right… he was just a year early.

That brings us to the following year, when I was a sophomore. One night, I came back to my dorm after dinner and found my roommates and some of their friends (including one of my roommates’ brothers, and the other roommate’s girlfriend) sitting around our coffee table with stacks of paper, pencils, and oddly-shaped dice.

“What are you guys doing?” I asked.

My roommate, Daniel Fernandez (a name you’ll hear pretty often in these columns), said, “We’re making our characters for Dungeons and Dragons. Wanna play?”

I scoffed. I don’t mean figuratively, I mean I very vividly remember literally scoffing at my roommate. “Nah,” I said (chuckling with just the right amount of condescension to illustrate that I still thought of Daniel as a friend, but had absolutely no interest in his silly game), “I’m okay, thanks.” And I went about my night, sitting down at my desk to update my MySpace page or lurk on the Facebook page of the girl who lived down the hall or whatever else I was into in 2007.

But as I sat at my desk, only a few feet from the coffee table, I began to overhear them talk about their characters. They went around the table and talked about their new characters, thieves and paladins and clerics, and about their backstories and personalities. And that’s when I really started to register what they were doing.

They weren’t sitting around and comparing their protractors, or whatever I thought “D&D Nerds” did. They were getting ready to tell a story.

All of a sudden, I was much more interested, and I started asking questions. And before I knew it, I found myself rolling up a level 1 human swashbuckler for my first game in Dungeons and Dragons (3.5 Edition).

I named my new character “Calvin Dugray.” The first name came from “Calvin and Hobbes,” the comic strip that I was obsessed with when I was a child. And I wanted my swashbuckler to have a bit of that over-confidence that Calvin had in that comic. My character, in my mind, thought he was hot stuff, and had no idea that nobody else agreed.

His last name, “Dugray,” was a reference to Tristan Dugray, Chad Michael Murray’s character on Gilmore Girls (another show I am a huge fan of). Tristan was sort of a roguish bad boy, and that’s another quality that I wanted Calvin to have. Or, more accurately, that I wanted him to think he had.

Add to that the visual of Errol Flynn (or Fandral from the Thor comics), and you had Calvin Dugray.

The following week, we played our first session, and I dove right into my new character. If you’re curious how Calvin talked, walked, acted, and thought of himself, just watch the first half hour of Tangled, before Flynn Rider gets any serious character growth, and you’ll get the jist.

And it was a hoot. To be fair, the only thing my character managed to accomplish that session was to get drunk, throw a rock at a troll, and get knocked out (while the other players did the heavy lifting of actually killing the trolls), but I was still hooked. I actually started keeping notes of the sessions – and wrote them in-character, as Calvin’s personal “Adventure Journals.” My thinking was that Calvin was convinced he was the next great hero of this world, so he was already taking notes to chronicle the undoubtedly-fantastic adventures he was expecting to have.

I even wrote an initial entry, before the first “adventure” began, to explain why Calvin was no longer with the crew of elf pirates that raised him. In the entry, Calvin noted that the Captain had begun acting strangely in recent days, and had asked me to leave the crew when I began to ask questions. I told this to Daniel, and his eyes lit up – I had unknowingly given him something that tied into the plot he was building, though he said nothing at the time.

But there was still some part of me that, on some level and for some reason, still thought D&D was kind of lame. So I thought I would do something to “offset” the lameness… specifically, to start drawing fan art of our characters. Based on whichever Marvel comic books I happened to be reading that month, I drew a comic book cover-style piece of art for each session of our campaign.

This is the cover I did for the first session, based on the cover for New Avengers #34 by Leinil Yu. Remember, for some reason, I thought this would make me seem less nerdy.

And just like that, my identity as a roleplayer was set – and honestly, it hasn’t changed much in the past eight years. I’m still not that into (read: good at) remembering or following the rules, but I’m very into my characters and their personalities and backstories. I still like to do art of our characters. And whether I’m a player or a Dungeon Master, I like having little props and handouts that I can have at the table, to help get people more into the game.

Throughout these blogs, you’ll hear a few more stories about Calvin Dugray, as well as some of the other characters I’ve tried my hand at playing. However, if there’s one moral to today’s story, it’s this: Anything can seem lame if you’ve never tried it. And because of that, it’s easy to dismiss something out of hand, without giving it a fair shot. So here’s my challenge: Try it. You have absolutely nothing to lose by trying new experiences. (Except for all of the money I’ve spent over the past eight years on miniatures, handbooks, battle-grids, and lots of dice.)

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Amazing, all those 3e reference pics. Nice drawing. I mean, really nice work. I started playing in 1989, after following a huge publicity the past years for the AD&D2e launch. as son as I was able to get those books I bought them, devoured them and wanted to play, BUT alas I was the only one who got the rules, so I became a "Forever DM".

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