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Source Ultimate Intrigue pg. 184
Due to its ability to convince people without using either deception or coercion—and risking their negative consequences—the Diplomacy skill is one of the most commonly used forms of persuasion in the Pathfinder RPG. However, it is also difficult to adjudicate in a variety of situations involving intrigue and combat.

Attitudes and Requests

Source Ultimate Intrigue pg. 185
The most consequential use of the Diplomacy skill is to change the attitudes of other creatures and to get them to comply with requests you make.

Attitude Adjustments, Personality, and Goals: One major trap in understanding the Diplomacy skill is the mistaken idea that attitude adjustments achieved using Diplomacy change a character’s underlying personality and goals. In fact, attitude adjustments are minor good impressions (or bad impressions, in the case of a disastrously failed check) that, per the Core Rulebook, last only a few hours by default. At the GM’s discretion, the adjustments may last for shorter or longer periods, depending on the circumstances. As such, a Diplomacy check to change someone’s attitude is mainly useful as a prelude to a follow-up request. It doesn’t alter the creature’s personality or goals.

For instance, if a cunning bard managed to convince the evil necromancer queen to become friendly with him, that doesn’t mean she will give up plans of world domination or change her deity from the goddess of undead to the goddess of beauty and love, but it does mean that she likes the bard now. Even without further requests, she would probably spare him if he pledges loyalty to her and if she thinks she can trust him. Even if she feels she can’t trust him, she might at least be fond enough of him to transform him into a loyal undead servant so she can keep him around. Attempting to convince the necromancer queen to give up her evil ways and cease her plans for world conquest involves much more than a Diplomacy check to change her attitude toward the bard. The bard would then need to use the influence system or the relationship system to become closer to the necromancer queen, perhaps engaging in a verbal duel with her or even focusing an entire series of social adventures around changing her perspective (see Social Conflicts).

Requests Are Not Mind Control: This is the biggest potential trap in understanding the Diplomacy skill in a typical game. Diplomacy’s main strength is the ability to make requests without angering the target, but that doesn’t mean that it works like mind control. As the Core Rulebook says, some requests automatically fail if they go against a creature’s values or nature. In this vein, it is important to remember that no matter how high a Diplomacy roll may be, the target still has free will and won’t accept certain requests. Even so, a character who declines a very high Diplomacy result should do so respectfully, as the high result means that the diplomat made her argument effectively and convincingly. For instance, a paladin who swore an oath to never unseal the inner catacombs of her faith’s central cathedral might apologize and explain that though the argument to do so was convincing, she unfortunately can’t violate this vow. A target who must refuse a request might try to honor the request in spirit, offering an alternative that might advance the same greater goal or doing a significant but still lesser favor for the requester.

Roleplaying and Skills: As you can see from the sections above, as well as the table of potential circumstances in the Core Rulebook, the nature of a request is crucial to determining its success or failure. Therefore, it is necessary to describe the request in order to attempt a Diplomacy check. A diplomat’s player can’t just say “I Diplomacy the guard.” The player must provide a specific request along with any rationale supporting that desire, even if the player or GM doesn’t want to roleplay the whole interaction in character. On the other hand, using Diplomacy to improve a target’s attitude is both more open-ended and less fraught with circumstance modifiers, so when strapped for time or out of ideas, it is fine to omit a description of how a diplomat manages to do so. Using the previous example of the bard and the necromancer queen, the bard’s request to spare a peasant so that she may spread word of the queen’s mighty army and cause other villages to surrender without a fight is quite a different situation than him saying, “Spare this peasant woman because killing her is evil and makes my goddess sad,” or even “Spare this peasant woman for me. Please?”

Gathering Information: The Diplomacy skill allows a character to canvass locations for information. Because this use of Diplomacy often produces similar results to those of a high Knowledge (local) check, adventurers might be able to attempt either one to gain the same information. In fact, adventures occasionally present a table of facts that either skill can uncover. Gathering information with Diplomacy actually involves spending 1d4 hours actively seeking the information and allows the character to retry the attempt to pick up additional information. When a PC fails at a Knowledge (local) check, the GM can give the character a second chance by having him spend time attempting to gather that information from others.

As per the Core Rulebook, some information is simply impossible to find via gathering information. The information that people know is typically limited to the area where they live, and is filtered through their biases. In a city on the brink of a race war between elves and humans, the information available among the upperclass human nobility will have a significantly different spin and tone to it than the information available in the elven ghetto, and the checks to gather information in those places would meet with circumstance bonuses or penalties depending on who was asking where. Thus, it is important to decide where a character is gathering information before determining what information they receive. Filtering the information through the biases of the community adds flavor and nuance to the world around the characters.

Finally, remember that gathering information is itself a conspicuous act, so others who are gathering information can usually notice it in turn. A typical DC for hearing about someone else gathering information should start at 15, and a character wishing to gather information clandestinely can choose to take a penalty on her Diplomacy check to increase that DC by the same amount.

Calling for a Cease-Fire: One of the first things that a potential diplomat might try in a combat is to call for a temporary cease-fire. The description of the Diplomacy skill in the Core Rulebook indicates that requests take 1 round or longer, and that shifting attitudes takes 1 minute. Since a cease-fire is a type of request, this would work fine, with the diplomat making the request over the course of a full round of combat and completing it just before her next turn. However, a character can usually only make requests of a target that feels at least indifferent toward that character, and the vast majority of battles involve characters that are unfriendly or hostile toward each other.

In this case, and in other instances of requests made to unfriendly or hostile characters, the GM should consider only allowing such requests that are couched in such a way that they seem to be in the target’s best interests. An unfriendly or hostile character certainly isn’t going to be doing the would-be diplomat any favors, but that doesn’t mean they will ignore an idea that is better for them than facing the consequences of the combat. Even if adversaries agree to a brief cease-fire to listen to the diplomat’s terms, they won’t let their guard down. Generally, they will also require the side calling for the cease-fire to make a show of their intentions by laying down or sheathing their weapons, dropping spell component pouches, or the like, while attempting Sense Motive checks to determine if the cease-fire is a ruse. Creatures that feel themselves to be at an advantage in the combat by virtue of a short-duration spell or other effect that would expire during a cease-fire almost never agree to a cease-fire, as it isn’t in their best interest to do so.