How to do Social Encounters in D&D 5e

First, determine the NPC's initial disposition. For allies of the party this can be Friendly, for any enemies that don't attack on sight (more info in Monster Desires below) it should be Hostile, and for everyone else Indifferent is fine. This can be further modified by how the PCs interact later, but never more than 1 step in a single encounter, so an NPC won't typically go from Friendly to Hostile or vice versa in a single encounter.

Next the players will actually engage with the NPC and RP out the conversation. This has no effect on the roll itself, but determines how the NPC will react to the roll based on how much they like the PCs from conversation first. Friendly NPCs will end up being more helpful, while Hostile NPCs may end up intentionally trying to hinder their plans. Take note of the NPC's ideals, bonds, and flaws and when the PCs say things that either appeal (making them friendlier) or conflict (making them more hostile) with their personality. The NPC Generator has a list of ideals, bonds, and flaws that you can use.

During extended conversation, the players may also want to make Insight checks to get more information about the NPC or how they're acting. This shouldn't function as a catch-all lie detector, but can instead be used to learn one of the NPC's motivations, ideals, bonds, or flaws. You could also make this a contested check against the NPC's Deception skill, or set a DC equal to 10 + Challenge Rating. Roll the PC's Insight check secretly, success reveals one of these traits, while a failure of 10 or more reveals a false trait. Knowledge of these traits can also be learned from close friends of the NPC, or from letters or journals using the same process.

After the conversation has played out, it's time for the actual skill check. First, determine the NPC's modified disposition, either moving up one (from Hostile to Indifferent, or Indifferent to Friendly) if the players roleplayed well and appealed to the NPC's ideals, bonds, and flaws, or moving down one (from Friendly to Indifferent or Indifferent to Hostile) if the they clashed with the NPC's personality. It can also stay at the baseline disposition if no significant progress was made in the conversation. This could also result in immediate combat if they were already Hostile.

The PC chooses which social skill to roll based on how they roleplayed and what they want to accomplish: typically Persuasion to trade favors, Intimidation to get them to back down, or Deception to trick them. If they were being assisted by someone else, then determine if that other PC's contribution will give the roll Advantage or Disadvantage, depending on if they got along with or clashed with the NPC's ideals, bonds, and flaws.

Compare the result of the roll with the tables below to determine how the NPC reacts to the skill check and whether or not they'll be helpful, or what extent they're willing to help with whatever the PC's request is.

A note on rivals: A result of 0-9 on the Hostile Disposition table may result in immediate combat, but when it doesn't (or when they survive) they will become a rival (see Downtime Events for rival activities).

You can also get a quick reference of the above at the Skill Breakdown.

Monster Desires

In order to parley with monsters out in the world, the PCs may need to fulfill that monster's desire. Doing so can grant Advantage on the above check, or may be required to parley at all if the monster is attacking. Note that "Hostile" means an enemy that doesn't attack on sight, like a condescending noble. Violent enemies therefore can best be made Hostile based on the rules above, and will likely need their desire fulfilled. Most randomly rolled monster encounters are assumed to be Violent unless they're a similar alignment to the PC, or you can roll a d8 on the monster personality table:

Depending on the desire, you may need to share a common language. A PC can make a skill check based on the creature type (shown in parenthesis), with a DC equal to 10 + Challenge Rating to learn its desire. On a failure, they'll have to guess. If the PCs are unable to fulfill the monster's desire, it attacks. You may want to make the PCs Surprised, or give the monster Advantage on its Initiative roll to represent the risk in parleying. Roll a d4 on the following table based on its type to determine its desire:

Need more help with your campaign? Check out all the other tools, generators, and articles: kassoon.com/dnd/

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