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Fighting monsters and navigating hazardous environments are only part of an adventurer's career. Characters will often find that words are a better resource than swords, spells, or brute force.
There are several schools of thought when it comes to handling interactions in a roleplaying game. Some DMs prefer to speak in character and adopt the mannerisms of a nonplayer character in the same way that an actor depicts a character.
Other DMs prefer to describe an NPC's dialogue, giving a basic outline of what an NPC has to say, rather than narrating the exact dialogue.
Players fall into similar camps. Don't try to force the players into one approach or the other. Just as some people like to play fighters and others prefer rogues, so too do different players take different approaches to portraying their characters.
No matter which approach you use, an interaction should be driven by the back-and-forth between an NPC and the characters. Dice should come into play only when you are unsure about a conversation's outcome.
Players who shy away from roleplaying prefer to let the dice do the talking for them. For such players, it's probably best to rely on the dice, rather than force that player to go against his or her preferences.
Calling for Checks
Adventurers don't need to make checks or enter into lengthy interactions when they buy supplies or order food in a tavern. Significant interactions in an adventure involve challenges and obstacles - persuading someone (or something) to do something he or she is not initially inclined to do, or not do something he or she wants to do. A significant interaction has objectives (things the characters want to accomplish) and obstacles (reasons why the NPCs don't want to acquiesce to the PCs).
When a character makes a firm argument, whether it's in support of an objective or an attempt to negate an obstacle, that's the time to ask for a check. Typically, the player characters and NPCs will exchange several lines of dialogue around each check.
Check or Contest? In most cases, you use checks for social interactions. Contests should come into play only if two parties are in direct conflict, such as in an argument, a debate, or a negotiation.
Picking a DC for an interaction check follows the normal guidelines for determining a DC, and it is important to consider the context of the check. A conversation is a fluid thing. Base the DC on what is happening in the moment. How has the conversation ebbed and flowed? What does an NPC think of the characters? A stilted, awkward exchange can turn a simple request into a high DC.
Think of whom the speaker is trying to sway or impress. You can do worse than start with an NPC's Wisdom score or Charisma score as a base DC. Use the target's Wisdom score for attempts to bluff or intimidate someone, while the Charisma score is a good choice in most other situations.
With that as a starting point, consider the NPC's attitude toward the speaker. A positive attitude can grant advantage, whereas a negative attitude or a faux pas can impose disadvantage.