Creating Encounters in One-on-One D&D: From Research to Execution

Tabletop for Two: Episode Four

Episode four of Tabletop for Two covers strategies and processes for researching D&D encounters. (You can learn more about scaling encounters here.)

This is another one of those topics where the sheer number of options of resources and creatures available can be overwhelming—that was certainly the case for me (Beth) when I was first getting started and trying to learn how to DM.

So, during our discussion today, we’re going to try to streamline that process for you as well as outline some of the elements you’ll want to consider during your pre-session prep such as the PC’s environment and your objectives for the encounter. 

Watch the Episode

Below, you’ll find our show notes and the tips we cover during our discussion.

Part One: Encounter Basics

First, what is an encounter?

Often, when we think of an encounter in D&D, we immediately picture a combat scenario, but we want to make sure to incorporate social and environmental encounters as well!

Types of Encounters

• Combat encounters
  • Best practices for one-on-one D&D—things to keep in mind
    • Use waves of combatants instead of sending several enemies in all at once
    • Action economy—the number of Actions each side gets per round. This takes into account spells that increase the number of combatants, like conjure animals, and bonuses like legendary actions.
• Social encounters
  • When planning social encounters, keep the desired outcome as open as possible to keep the focus on the PC and their goals.
• Environment encounters
  • Storyteller’s tip: You don’t need to have a solution picked out for encounters or locations, whether it’s a haunted forest or a dungeon. This openness keeps the PC’s problem-solving open and fluid, and it lets the DMPC contribute as well without it being the DM providing the player with the “answer.” Then, as the DM, it becomes your job to roll with the “yes, and’s” instead of telling the player why their cool idea won’t work.
• Boss fights
  • Changes in the stage, use evolving terrain
  • Mix up the win conditions! Perhaps someone or something besides the PC is threatened with failure states?

Unique Goals for Encounters

When we ask after the objective of an encounter, what does that mean? What are some possible goals for an encounter?

• Set up/introduce an “enemy” for the party (you can find more on opponent motivations in episode three of Tabletop for Two!)
• Preventing an escape, rescuing people, stopping a ritual…

Part Two: Planning Resources

You can find a list of planning resources for new DMs and encounter prep processes here.

Step One: Narrow the Field of Options

• Easiest question to start with: Where do you want the encounter to take place? 
• You might also consider creature type if you want to narrow things down further. 

Favorite Resources

• Dndspeak—lists of 100 (for d100s) like 100 activities for a festival, 100 mushrooms and their effects, 100 magical landscapes, etc. 
• Sites like Roll20, 5thSRD, and D&D Beyond have lists of creatures by type, which can be another way of planning encounters
• You can also use sites like tribality with their shorter lists for region-based encounters along with rationales behind why you might want to use a creature in a particular setting 
• Once you’re further along in the process and trying to figure out what to do with the creatures you’ve selected, you can check out The Monsters Know by Keith Ammann, who is working on his fourth D&D book at the moment! He has two out now, TMK and Live to Tell the Tale. He also has a new supplement out on DMsGuild called “The Buddy System” which has tactics for Beast Masters. You can preorder his new book of monster tactics, MOAR Monsters Know What They’re Doing. 
• If you’re using NPCs in your encounter, definitely check out Fantasy Name Generators. Emily’s work is absolutely outstanding, and she has lists for fantasy locations too! My new favorite is fantasy bookstore names like “Read ‘n Mead” and “A Likely Story.” 

We hope you’re enjoying Tabletop for Two and find the videos and show notes helpful! Do you have any favorite resources that we didn’t mention here? What are your favorite questions to ask yourself when prepping an encounter? Let us know in the comments below!

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