Talk about getting outside your comfort zone. This is so far outside my comfort zone that it’s on a completely different planet, with a poisonous atmosphere, crushing gee forces, with a comet heading directly for it.

My First Roll20 Game Wasn't Terrible

2,949 words.

My First Roll20 Game Wasn't Terrible

Talk about getting outside your comfort zone. This is so far outside my comfort zone that it’s on a completely different planet, with a poisonous atmosphere, crushing gee forces, with a comet heading directly for it.

I signed up to play in a game of Dungeons and Dragons on Roll20.

I write this story both so that I remember it, and as a minor public service, because I found it rather difficult to find helpful Google results describing good experiences of starting out playing Dungeons and Dragons (or anything else) on the Internet.


I’ve had this thought for several years now: “It might be fun to play some tabletop role-playing games. I remember them being kind of fun as a kid, and it looks kind of fun when I see people playing on these trendy D&D streams, even though I know 95% of what I’m seeing is Hollywood production values.”

But something has been stopping me all this time: I don’t know any other humans, certainly no one that plays tabletop games. The only other residents in my house right now are cats, and they haven’t expressed much interest.

I have some family members that at least used to play D&D, but I don’t live near them and they aren’t all that Internet saavy, so that’s not really a viable option.

Occasionally I search for what others do in this situation. The usual advice for getting into this hobby if you’re like me–a socially isolated recluse with no friends–is to find a local game store and inquire within, because they’re supposed to have groups and workshops and whatnot.

But local game stores aren’t really a thing where I live. Besides the entire issue of the pandemic destroying most of the local retail business economy, I don’t know of any such stores within somewhere around a 45-minute drive. I doubt I’ve been in a retail toy/hobby store since the 80s.

There’s also the minor fact that I don’t really like to leave my house or drive to strange places or interact with other people. It’s kind of exhausting. And that was before various novel coronaviruses made such pursuits potentially dangerous.

Enter Roll20

So that leaves only the world of remote gaming over the Internet. There’s only two popular places I’m aware of for role-playing on the Internet: Roll20 and Fantasy Grounds. Roll20 is free, Fantasy Grounds isn’t. Not a hard decision.

Sometimes I go on there and search for games to play in. It’s incredibly intimidating. You know how everyone hates to search for a guild in an MMORPG and just gives up and plays solo because no guilds are ever a good fit? (That might be just me.) It’s like that, except a thousand times harder.

Well, this past Friday, I went to Roll20 again and searched to see if there might be a game on the weekend. I don’t know why this week was the week I did this, of all the weeks in the past couple of years. It just happens to be a week when TTRPGs are on my mind. It might also be because I don’t have any video games I’m all that interested in playing at the moment.

I set the search parameters to find only one-shot D&D 5E games friendly to beginners.

One of the first results looked like a jackpot: A “beginners one-shot” listing for the very next day, specifically for people who are brand new to tabletop gaming and Roll20, to teach how everything works.

It sounded too good to be true. Who on the Internet is actually friendly and accommodating and willing to teach new players? It’s unheard of, completely ridiculous. It can’t be real. It had to be a scam to steal my identity or credit card information. That’s really the purpose of the Internet, after all: To gather data from gullible people and sell that data to advertisers and criminals. There’s no other reason for the Internet’s existence anymore.

There were only four slots to fill for this one-shot game and I imagined they would go fast.

Making A Roll20 Account

Despite knowing full well that I was walking directly into a trap that would ruin my life and finances forever, I figured I was never going to get anywhere if I didn’t take a chance, so I went ahead and made a Roll20 account. Not surprisingly, you can’t play on Roll20 without first making an account. It’s the only way that web sites can make money by selling your data to advertisers and criminals.

I was wary of entering personally-identifiable information, but I set it up with my real name email account, because it seemed obvious that the chances of people trusting me (also a complete stranger to everyone else on the Internet) would be considerably higher if I didn’t use a name like “burner-account-haha-483.”

And besides, it turns out that googling my name on the Internet no longer only finds me. Unlike the 90s, there are now tons of other people on the Internet with my name. Also, I’m not that concerned about being associated with Roll20 and D&D anymore. There was a time in my life when I would have been mortified for people to know I played video games or tabletop games, particularly any work colleagues, but that’s not much of an issue where I currently work and there’s a good chance it’s the last place I’ll ever work anyway.

As I was making my account, I noticed that Roll20 pulled in the avatar from my GMail account, which was roughly, I want to say, a million years old, from about six houses and four lifetimes ago. So I went outside and took a couple pictures of myself with my phone camera and changed both my GMail and Roll20 avatars.

As a side note, I look really old now, and weirdly a lot like my older brother. I’m not sure how I feel about any of that.

Job Application

I posted a message to join this beginner one-shot game. I don’t know how things normally work on Roll20–I assumed there would be a button somewhere that said “request to join this game”–but in this case, the GM asked people to introduce themselves with a post. Each game listing has a little old-school-style message board attached to it. Remember message boards? So quaint.

It sounded sensible to me. If I were a DM asking for players, I would also want them to surpass at least the minimal barrier of entry of saying hello in an inoffensive way.

So I posted a little note under the two other folks who had already asked to join the game, writing a little bit about myself. Nothing too verbose, just a few sentences conveying the notion that I’m at least high-functioning enough to write complete sentences and that I understand the general concept of not being a jerk in the very first communication with another human being.

Of course I immediately second-guessed my decision and regretted it. But no turning back now, I guess. No good deed goes unpunished. All good things are for other people, not you, and you’re destined to die alone and in horrible pain because nobody loves you. I think that’s how the saying goes. Something like that.

Not much later, less than two hours in fact, I received a message on the site with an invitation to the game. I accepted it. Definitely no turning back now. Unless I just didn’t show up, of course, which was the emergency rip-cord option that I kept in the back of my mind.

Getting Ready

For this one-shot game, the GM didn’t require us to have anything except a link to the basic D&D rules, which is a PDF file describing, well, the basics. The barrier to entry for this game could not possibly be lower: Just show up on this web site at the appointed time (6:30 PM on a Saturday, in my case) and learn the ropes as you go.

I still didn’t fully believe it. At some point, I expected it to turn into a catastrophe. At some point, I expected the GM would launch into a sales pitch for condos or cryptocurrency or something.

I wasn’t required to have anything, but as it happens, I recently bought some D&D 5th Edition rule books on a whim (and also Traveller and Call of Cthulu rule books). I’ve also watched enough D&D streams and played enough Solasta: Crown of the Magister that I think I have at least a basic understanding of the core concepts (action, bonus action, movement, advantage, disadvantage, blah, blah). So I’m not completely new to this, but I would definitely label myself a beginner. What they don’t show on the streams is the part where they roll a character and choose their abilities and all the boring stuff.

The difficult part for me has never been understanding and applying the rules of the game, though, it’s, you know, the human interaction. “Role-playing.” Role-playing wasn’t really a thing back in the 80s. We just murdered kobolds and orcs and picked up their gold. Character backstory? Telling a story? Cooperatively with other people? That kind of stuff didn’t exist. The story was always, “Go to the dungeon and kill everything.”

The Longest Saturday

Here’s a thing about me: Any disruption in my normal daily routine, particularly with an event that’s unfamiliar to me, creates a massive tidal wave of anxiety that lasts until the disruption is over. If I have an appointment on Friday, for example, I’ll start preparing for it and worrying about everything that could possibly go wrong with it, starting on Monday.

So it was a blessing that only about 30 hours would need to pass between the time I saw the Roll20 listing and asked to join the game, and the game itself.

But there was an entire Saturday to fill, where my brain was screaming at me on repeat, “RED ALERT YOU’RE DOING A THING WITH STRANGERS ON THE INTERNET TONIGHT THIS IS THE WORST SCENARIO IMAGINABLE, YOU KNOW I DON’T KNOW HOW TO SOCIALIZE WITH HUMANS AND EVERYONE’S GOING TO KNOW, YOU’RE IN SO MUCH DANGER.” I’m old enough to recognize that this is a thing my brain does and have a basket full of tools and strategies to deal with it, but it’s an effort.

To add to my stress, on Saturday morning, I only saw my own name listed as part of the game. This was some cause for concern. But by 2 PM, three other people were listed in the game alongside me. (Plus the GM.) Whew. If you’re keeping score, the game filled up in less than 24 hours. But it was a big relief to see that I wasn’t going to be the only one that showed up.

Game Time

So at the appointed hour of 6:30 PM, I clicked on the “Join Game” button. It turned out I was the last person there, and should have gotten there earlier. Oops. Then it turned out my whole system melted down for some reason and I had to reboot. I was trying to play on my gaming PC, on which I had just installed Firefox, because Roll20 said they really only supported Chrome and Firefox. I also had an idea to record with OBS so I’d be able to pull some screenshots for this blog post, and I think that interfered somehow. After rebooting I turned off OBS and tried again, and it worked.

Roll20’s voice chat didn’t work for some reason, so we moved to Discord for voice chat while using Roll20 for the map and character sheets and rolling dice and stuff. The GM explained that failed voice chat is a common problem on Roll20, so he had a Discord setup just for that situation. It was a bit of a hassle for me because the link provided kept wanting me to create a new Discord account instead of using my existing Discord account, and there was a bit of confusion and panic as I tried to remember a different email account to make a new Discord account, but eventually I got it straightened out.

I don’t really know where everyone else was from, but the GM had a slight European-ish accent that I couldn’t place, one player said they were in Canada, and another player said they were in Australia. You can never really tell but based on speech vernacular it seemed like a range of ages going from “younger than me” to “a lot younger than me.” But it was fine. From the YouTubes and the Twitches and whatnot, I’m used to seeing that everyone playing D&D is roughly half my age. Everyone was polite and friendly and upbeat.

Then the GM walked through the whole process of creating characters with us, explaining how everything worked on Roll20. It was more like a work training seminar than a game there for the first couple of hours, which is exactly what was expected and what I wanted.

I made a plain old Dwarf Fighter. The others made a Rogue, a Wizard, and … a Sorcerer I think? I wasn’t really sure. If I ever do this again, I need to be more militantly disciplined about writing down names and races and classes. (Roll20 didn’t seem to have any easy way for me to find out who or what the other members of my party were, which seemed a bit silly. Using Discord, it was somewhat difficult to mentally connect the sounds of the voices talking to the characters on the map.)

After making characters, we went through a teeny tiny homebrew (presumably) scenario where we were thrown into a classic locked room and told to do some stuff to get out. It was awkward at first but it got a little smoother toward the end. None of us really knew what to do so the GM had to prod us a lot, which I imagine is normal for new tabletop groups who don’t know each other or anything about each others’ expectations. The scenario didn’t make any narrative sense, but it didn’t matter. It was like a contrived tutorial quest before a game starts, where you just get a small taste of how a tabletop game works, and in that capacity it worked fine. Some NPC interactions, some combat, some rat-throwing, the usual stuff.

The heroic efforts of my Dwarven Fighter included shooting an elemental with a crossbow, expertly throwing a rat into a well (“you’re the Michael Jordan of rat-throwing”), and rolling a natural one on a medicine check when attempting to re-assemble two halves of a bisected corpse, resulting in their mis-aligned body screaming in agonizing torture for the rest of the session. It was funny. You had to be there.

The whole session lasted about four hours–wait, no, five hours–which was an incredibly long time for me to be at a computer, and about two hours longer than I expected. Fortunately there were a couple of breaks and I used my wireless headset so I could move around and stretch and mute at will. It wasn’t as hard on my back as I feared it might be.

I’m certainly not in any position to evaluate dungeon masters, but I thought he did pretty well, and he actually complimented us on being the best group of players he’d had in a while. I mean he probably says that to all the players, but I thought it was a decent group of players too. Everyone was polite and seemed to enjoy themselves. Just regular folk, all of whom had a decent understanding of the intangibles that make group voice communication tolerable (which is really just one thing: don’t talk over top of other people). I don’t know if I’d want to sign on for a six year campaign with them, because I think we were all different player archetypes, but it was fun enough for one night.

After It Was Over

I went to bed almost immediately after it was over because I was up way past my bed time. I felt relatively good about myself for taking a chance on something and actually enjoying myself. I was somewhat stunned that it went so well, no catastrophes at all.

The next morning I woke feeling like I’d made a horrible mistake and did everything wrong and embarrassed and humiliated myself. But, you know, that’s normal for me. It takes time for my brain to process and sort these things out.

What I Learned

I’m not particularly great at role playing, certainly not in the company of strangers, but I’m a lot better at it now than I was when I was twelve. I got the impression that the idea of a dwarven fighter who was ostracized from his clan because he just wants to live in the woods and paint was a lot funnier to me than anyone else.

The fact that everyone’s microphone comes in at different volume levels and there’s no way to adjust it on the receiving end drives me literally insane. In the future I’m going to have to investigate to see if there’s any way to deal with that.

As for Roll20 as a technical product, it’s pretty cool but it seems a bit janky compared to what I’d expect from a web site in 2022. But, you know, it’s free. (It’s also riddled with ads for upgrading to non-free subscription plans.)

Would I do it again? Probably. I think I stumbled into the optimal strategy: If I decide I want to play on a Saturday, look for a one-shot game on Friday.

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