overgeeked
Open-World Sandbox
I look at that in the light of "even the most repulsive personality can sometimes make a point that is uncontestable." A character with a 3 Charisma is going to have enough mechanical penalties, I don't see a need to also penalize the player for wanting to roleplay.
Agree with handling it with role-playing.
Although, I don't require the player to act out in character. All the player needs to do is state what they want from the interaction and how they approach the NPC. We can imagine what the PC actually says to the NPC through the filter of the PC's Charisma. To me, it is player skill to determine how their PC approaches the NPC. Do they use flattery?, intimidation?, deception? to achieve their intent... this is not something I just handle with a roll.
I approach Charisma checks backwards (it may be my experience running older edition games*). I have a Charisma roll at the start to set a baseline disposition (if it is not clear already) and then have role-playing determine the outcome of the interaction.
*This comes from the concept of the Reaction Roll, where if you don't know ahead of time the reaction of an npc/monster, you roll to determine their initial reaction. Which then determines how close to hostility the npc/monster is.
I do much the same. If I don’t know how the NPC feels towards the PCs, I’ll make a reaction roll to start things off. But I really like the mixed approach from 5E’s DMG on handling interaction. Conversation between DM and player to possibly influence the NPC, then a roll—if necessary—to determine whether the NPC goes along with the request. The player can RP the character in such a way as to make success automatic or impossible. But you don’t skip over the roleplaying and go straight to the roll.