Chasing the Dragon of Free-form, Play-by-Post Roleplaying

26 Jun, 2026

Before I get into what I want to write about, I just wanted to say that I know I haven't posted in quite some time but I am still working on my own personal fantasy heartbreaker, Covenant & Empire. I have just recently completed my teaching credential and that involved 80 hours of unpaid labor per week in the guise of "student teaching" as well as a full courseload of night classes -- my brainpower was wholly dedicated to that! But, now I'm on break and seeking employment so I have time to think about elfgames again.

Being back in school after a few years has been making me really nostalgic, so come with me down memory lane, if you please...

Something that I have been thinking about is how much I was into reddit as a quasi-forum back in high school. My friends and I ran a somewhat popular fandom subreddit that got into the hundreds of thousands of users and is still going on to this day -- though we have all stepped away from reddit.¹ This was back when I was in high school and while I had a strong core group of friends, no one was really interested in the same fandoms as I was and, if they were, not in the same way. Skyrim was released my sophomore year, for instance, and in the leadup to the release I was getting more and more invested in The Elder Scrolls as a setting² and roleplaying in general; I very clearly remember thinking about who my character was, and how they fit into the wider world around them. I was getting more and more involved in online fandom because, while my friends did enjoy Skyrim when it ultimately released they were much more interested in getting the coolest armor and weapons and killing everything that moved and having as much gold as possible. I was a very frequent user of the TESlore subreddit, and one day I happened upon a post for a roleplaying/fan fiction writing group with its own subreddit. While I did enjoy discussions on forums, and eventually reddit, I also began to use IRC around this time for more frequent, informal, and immediate chatting with other nerds. What initially drew me into the group was that everyone seemed to have very similar ideas about the more granular parts of the setting of Tamriel that the games don't really touch on. That, and the idea of living in another world, as another person, was very attractive to myself as a teenager. There was also a relatively high level of effort required to get in -- you had to submit your character to an out-of-character sub for approval; everything on the actual subreddit was in-character only.

This was not the first time I had ever encountered roleplaying online. I had been on other forums that had similar play-by-post setups but there was no real consistency. With the moderators of the TES RP subreddit, however, there were some really strict non-negotiables. For one thing, the location they selected was far to the south of Skyrim -- so no one really had an easy way to excuse connecting themselves directly to major characters from the (then recent) TES V. Another was that the premise was that every character should be original, but could not be connected to any of the protagonists in any way. No Dragonborn walking around, no Nerevarines, no Agent, or their children, siblings, etc. The other really brilliant thing is that there was some very strong, unspoken guidelines that the games should heavily inform how the roleplaying was carried out, but they are by no means the definitive versions of the world of TES. My previous experiences with forum roleplaying were not so...comprehensive. There were scene kids walking around next to space marines and level 35 elf rangers. For all intents and purposes it may as well have been anything goes. It didn't appeal to me at all. But since we all had a good idea of the setting,³ and the mods were just rigorous enough with the approval process that it took at least some effort to get involved but not so tough as to keep people away, it created this really immersive vision of my beloved fantasy world in my mind. I of course wrote up a biography of my go-to character from the games, sans any great, world-saving destiny and hit submit. For the next few years, I was on every day (almost). Part of what made it so good is that, on our own, we decided that each post should contribute to some kind of storyline. There was never any kind of post that was just general, aimless roleplaying. Most people initially stuck to their own backstory, and eventually dynamic interactions would occur that caused interpersonal drama. A few years in and we were coordinating big story events, but the collaborative nature of the thing meant that it always had some kind of surprises. It was a little like we were co-authoring a huge network of fan fiction -- and sometimes we even ended up writing posts that were just single stories in and of themselves, trying our best to write interesting, character-driven stories.⁴

As all things go it began to wind down. I want to say about five years in was when the end was nigh. At that point we had all been chatting almost daily, even eventually playing video games together, some people even met up once or twice in person. But the biggest names were getting a little too big -- part of the reason it fell apart was that the storylines got too intricate. We eventually allowed people to have multiple characters and I think that artificially inflated the user count and kept things going longer than they should have. I wrote my character out, pretty well for my capabilities even back then; he was a bosmer and went back home to try and foment revolution against the Aldmeri Dominion, effectively walking off into the sunset. I still check in every now and again and there are a couple of posts made each year, some with familiar usernames even still, but it will never get back to what it was. I did come back out of retirement shortly after with a new character, but it wasn't to last because around this time was when I began to really get into actual RPGs.

All this to say, I think that roleplaying over text is much, much easier and immersive for me. I do enjoy it in person whenever I get the chance, despite enjoying the dungeon-crawling aspect of OSR games but when I have to think on my feet it can feel a little awkward. Writing gives me time to think, not just about what my character will do but also about how they would say what they say and be more thoughtful about it all. Another thing that's amazing is that there were no real "rules" other than some commonly agreed upon guidelines. We played out epic battles, tense chases, and daring escapes all without dice or any real rules. While I am still working on the rules of Covenant & Empire the takeaway should be that I can write all the rules I want, there's just no way to make that lightning in a bottle. It's my hope that, when I do run The Third Dynasty that between sessions I can get people to roleplay over a Discord channel, I know my friends who play games and I think that may be a hard sell. I think it would be a lot of fun to handle downtime in that really loose, free-form way just like I did all those years ago but, again, it was lighting in a bottle.

I have played in several really amazing roleplay-centric campaigns over the years, but nothing will ever get close to my time spent on that island in the Topal Bay. If you've ever experienced something like what I'm describing, I'd love to hear about it. You can get in touch with me on Bluesky, or on the OSR Discord server. Maybe you've successfully tried something like this in your own campaign; maybe you think mixing this kind of RP and a sandbox campaign is a bad idea -- I'd love to hear about that too!

For now, keep your eyes on the skies.

Footnotes