dreaded_beast said:
so how do you handle it? during every encounter, do you roll your diplomacy or do you mainly role-play it? what happens if you roll a 1?
I can say how I THINK it should be handled; we're not always successful in handling it this way
Our group loves the roleplay, too: we can spend whole sessions discussing cosmology with NPCs, or interacting with house guest NPCs, or trying to finagle our way into some sort of poitical/theological deal with high-ups in a city.
Generally, we don't roll for things. As a DM, I try to keep folks' charisma and cha-based skills in mind: when the diplomacy-happy bard tries to weasel information out of the noblewoman villain, I'm a lot likelier to give him information than when the surly barbarian tries the same trick, even if the bard's player isn't as good a talker as the barbarian's player.
However, if the bard character tries to get away with, "Uh, tell me information, I've got +15 diplomacy," I'd probably not give her as much information as, if the barbarian character launched into a clever yet in-character gambit, I'd give to the barbarian.
We might sometimes roll for things. If we did, I'd ask folks to roll before the roleplaying happens, and I'd use the results of their rolls to inform the NPC actions in the scenes. The bard who rolls a 25 on his diplomacy check finds his every compliment met with a blushing smile, his every question answered eagerly, his suggestions favored; the barbarian who rolled a 3 finds herself largely ignored and cut out of the conversation, and if she tries to force people to pay attention to her, she'll be met with icy stares.
I'd recommend talking to your DM about it and seeing if he can make the social skills more relevant in the game. Just make sure you don't botch your own diplomacy check

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Daniel