Quests involving persuasion

Surprisingly nobody has brought this up, but many modern MMOs and single player RPGs have quest systems where there are several ways to achieve a goal and one of them is persuasion. The way a lot of them work is by relying on a Speech skill, ie Skyrim. Interactions in Skyrim also depend on your gender.

That wouldn't necessarily be bad, completely, but I would also enjoy a situation where you actually have to guess what will persuade the person in question. In some cases that might mean talking to other people and associates. In some cases it might be knowing his personality. Someone might readily take a bribe, while another person might see it as an insult. This could also be tied to the virtue system.

Another game that comes to mind is Darklands, an old but good game. There are several instances where you have to make a choice how to proceed. For example, if you want to get into a gated city, you can choose simply paying a toll, persuasion, sneaking in, using alchemy to create a distraction, praying to a saint, and so on. (Any Ultima fan who hasn't played Darklands -- Go play it!)

 

GW2 had this but it seemed half implemented.

Assuming there's a virtue system in game, this would be the obvious choice. Although this gets interesting if you lose in one virtue to gain another. e.g. that was Compassionate, but not Just