First Time DM: My Final Entry in the Series

I’m sorry. It’s true. This is the final entry in the First Time DM Diaries because… I’m no longer a first-timer! I had my trial by fire in a streamed actual play charity one-shot with a homebrew adventure. And may I just say… going forward I may never advise anyone else that all of those elements combined should be their very first time solo in the DM seat.

Let me be clear, the game was an absolute delight, we had a lot of laughs, there was wonderful reaction from the viewers, we raised over $2,000 for The Trevor Project, and barring some mild technical difficulties on both my and the producer’s ends, it all went off without too many hitches. Success, job well done, pat myself on the back, etc.

Gilded Gals – a Charity One-Shot for Kobold Press to Benefit The Trevor Project

I will forever live in that “They said they had a good time, but did they, really?” place of insecurity and impostor syndrome, but I also have to admit that at the least, I’m pretty good at being an impostor and had them all fooled. I HAD EVERYONE FOOLED! 😂

To quickly recap my earlier entry, the Gilded Gals game came about from a stray idea during a PAX Unplugged panel for getting some “old biddy” characters together for a one-shot, they asked me to run it, I said yes despite my inexperience, and again, I have to say, we had a blast!

I wrote up an adventure that had elements of classic sitcom situations, a bit of Willy Wonka, a nod to other older women TV characters (Jessica Fletcher, Hyacinth Bucket, Enda Garrett, Pearl Shay), and general nonsense along the way. Having shown my outline to some writer friends, I was told that I wrote too much, which is the right amount for me, to be honest.

I didn’t make it too complicated in terms of puzzles or combat, and I was terrified we wouldn’t get to do everything I wrote–we didn’t. However, I knew that no matter what, whether I had them on rails or whether I leaned back and let them improv their way into the plot, it would all work out.

And it did! We had it set in The Old Margreve Forest in a sort of retirement community (think Shady Pines), and since I could craft the adventure for these characters, it was really focused on what they said and did to shape the world around the story I planned to tell. As I said, we didn’t get to every part of the adventure that I planned but that was due to both good and bad things…

A frozen moment of peace, early on, before the CHAOS.

When you’re streaming, there are so many things that you have no control over. We had a fantastic producer, but sometimes things just happen. In this case Zoom decided to be dramatic and had been having server issues. The internet connection was playing up, and in my case, my internet just said “I would prefer not to.” and dropped mid-show. 😲

Here’s where having a wonderful cast and great producer are really to your benefit. They vamped. They vamped extremely well. I was panicking, sending messages to Discord on my phone, waiting impatiently for the connection to resume and hop back in the call, but my players just handled it, in fact going on to decide how they were going to handle the plot threads I’d given them before my sudden disappearance.

The paraphrased saying, “No good Dungeon Master’s plan survives first contact with the Players,” is all too true. Now add in the blessing and curse of all charity one-shots: donation incentives, and you’ll find that your plan never stood a chance at all. I don’t want to say people were too nice, but we allowed for charitable donations to affect the game vis-à-vis dice rolls, wild magical effects and the one that made me really think on my feet: magic items.

Blue tea?!

Kobold Press was kind enough to provide us with details of their Fantastical Food and Beverages from the Vault of Magic and we set it up that players could roll on a table and that would determine what they got. One item in particular: Blue Rose Tea.

The petals of the Blue Rose can be brewed into a tea. When you consume a dose of this tea, you get a glimpse into the future. This Effect works like the Divination spell, except the answer comes to you in visions rather than from a deity or its servants, and you can ask a single question concerning a specific goal, event, or activity to occur within 14 days.

Nothing could have prepared me for the players being able to have doses of a potion that would let them see the future, that I as the DM had to answer truthfully.

“It was at this moment, that he knew… he fucked up.”

If you watch back, you might see the panic on my face while reading the item description, but I managed to give truthful vague answers to the specific questions they asked without giving away anything.

There were still parts of the adventure I wrote that we didn’t get to, and there were other parts I didn’t bother to write except just a big vague concept in brackets because I trust these players. But in the end, I feel like I learned a lot about my style of running a game, handling players and keeping the story going. I tried to give the story that blurred line of a feeling somewhere between 22-minute TV episode and D&D adventure and I think I did OK.



A huge thank you to Meagan for asking me, to Vee, Dot, and Noura for trusting I wouldn’t fold under the pressure and to Jordan for running things flawlessly behind the scenes. As much as this is about me and my First Time DM experience, it was a team effort of cast and crew and that can’t be said enough.

Will I do it again? Maybe. No promises, I did have a good time, and we did say, “Hey it would be great to get this crew together again,” so we’ll see what happens in future. And as anyone knows, I’ll say yes to just about anything for charity so… who can say? 💖

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