From One Dungeon To Another: An Unexpected Turn

Salutations friends and it is time for another edition of mine and Jake’s collab series From One Dungeon To Another, a series of articles where my DM friend Jake Hutton and I both write about the same topic but from two totally different perspectives! We’re taking a bit of a break from talking about our “favourites” and decided to go down a more experiential route. We will be talking about those moments that we totally felt unprepared for and our quick thinking turned the sitaution into something totally awesome, and when it turned into something not so awesome…

Now, as a disclaimer, I have much less experience as a DM than my friend does so I’m sure I still have a lot to learn and experience. We thought it would be interesting though to see how an inexperienced DM like myself is dealing with the unexpected events (in hopes to give you new DMs a bit more confidence from my mistakes) and how a more experienced DM like Jake handles curve balls like a pro – so be sure to check out his article too!

Now let’s start with the negative… A moment of shaaaaame:


Now if you read the second post in my “Ravensend Guild” blog posts, outlining the adventures of my D&D campaign, you’ll know that my group ran into a tough battle with a group of goblinoid creatures. Half way through the battle, the group decided to retreat, but try their best to capture one of the hobgoblins with the intention of gaining information before going.


They spent several rounds of combat yelling at each other to not kill one of them to capture them, every character hitting that particular hobgoblin indicating nonlethal damage with the butt of their hilt, or aim for nonlethal points. They finally managed to bring one of the hobgoblins down to zero. As they continued to fight the remaining 3 creatures (one other hobgoblin and two goblins), the second hobgoblin decides to kill the unconcious hobgoblin with a death blow, preventing the group from capturing him.

Yes, they were pissed. My rationale of the situation: the only way every character could indicate nonlethal damage is communicating it some way in combat, especially if their fight intention was to kill. There was a change of strategy communicated between players. I took that as a communication within combat in character, meaning this hobgoblin who can understand Common would know the intention of their enemies. Being the lawful honorable hobgoblin they are, they didn’t want these outsiders to know their plan, just in case their fallen comrade spilled the beans… So would it be more lawful to allow their comrade to live in hopes that they will make it out of this alive (not likely seeing as it was 3 vs a group of 5)? Or would it be more lawful to eliminate their chances of discovering a secret, even if it meant killing an ally?

Probably the first.


Truthfully I panicked. I already had a portion of the adventure planned for how they would discover the secrets the goblins held in the forest. I didn’t anticipate them trying to capture one of them (which was definitely a mistake on my end… OBVIOUSLY they will capture and torture an enemy to get information, right Jake? ;)). In the end though, I realized my mistake and I regretted it. I just tried to railroad them onto the path I wanted. Luckily one of my players thought of the great idea of sticking around the area stealthed, and launch another sneak attack on the remaining goblins after they felt safe again. This was my redeeming moment! So in the end they did capture a goblin, not who they originally wanted, but they got one.

I suppose in the end it turned out okay, but only because one of my players was stubborn and determined to get that information. I still have a lot of D&D moments ahead of me, but I do think that is one of the moments I regret the most in the very few sessions I have done so far.

Now for a positive! Yay!


This moment actually happened in a one on one session I did with my boyfriend. I was nervous about being a DM and he was nervous about being a player, so we decided to do a small one on one session to warm up and gaining a bit more confidence before we do it in front of four other people. This was something I didn’t expect AT ALL, but I have to say it may be one of my favourite moments still.

Upon entering this new town, his Bard character asked if there was a music store, somewhere that sold instruments. My thought process was “DON’T SAY NO! SAY YES AND! YES AND!”, plus it was a big enough town to probably have some sort of shop that had music. I pointed him in the direction of a humble halfling lute maker, his wife, and his shy adorable son, who then led him to a tavern that his wife’s brother, a fellow lute player, performs at. I didn’t even have a name prepared for the tavern, that is how big of a tangent this was.

Once he got to the tavern, he met with a half orc adventurer who had very little interest in talking to anybody other than this pint of ale…. And that cute human woman talking to that half elven woman. The Bard wanted so badly to become this Half Orc’s friend that he insisted on talking to the ladies on behalf of the shy grunt. He charisma checked his way through flirting with the ladies and even sang them a lute rendition of Taylor Swift’s “Shake It Off”, which he actually did.

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This entire exchange from the music store to the tavern happened before we even got to the second bullet point in my notes (the first being: city of Ravensoul: streets are busy since all of the businesses, taverns, shops, etc. are all concentrated in this central part of town – very crowded with patrons and tourists and citizens).


This is the first page of my notebook for this particular session. The majority of all of these events happened before he even encountered the NPC Fae.

This session just turned into a silly fun experience for both myself and my player. I came up with some great NPCs that can be used later on in the campaign (since this is the main city so far) and got a really entertaining encounter out of it. This moment is a prime example of using that good ol’ improv trick “yes, and…”. I was able to give my player the freedom to do whatever he wanted and it led to some really great light-hearted moments.

Looking at these two unexpected events in my campaign, I can truly say that D&D is not about the players or about the DM. It is about the players AND the DM, trying to listen and say “yes, and..” to each other. We are building this story together. There will be learning moments and memorable ones with any unexpected reaction. Welcoming the unexpected, no matter how unprepared you feel for this particular event, will feel more fun in the long run. So let them capture the hobgoblin, or find a niche shop in the town. Even respond with a shakey “Uh… sure?” My personal favourite is, when a player asks if they can do a certain thing, I respond with “Well… You can certainly try.”

Don’t forget to check out my friend Jake’s post about this same topic right here! And while you’re at it, check the rest of his blog out too! I promise he has some very insightful thoughts, or at the very least, a very fun story.


2 thoughts on “From One Dungeon To Another: An Unexpected Turn

  1. Pingback: From One Dungeon to Another | theroomfillswithwater

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