Walks with the Snails
Erudite
That's a really good point I hadn't thought of before. Dialogues in RPG's are rarely challenging, if they have any impact at all, it's just a matter of choosing the nice guy options and getting people to like you. Mainly they're there just to add flavor.
I think one way to make things more challenging is to offer mysteries to solve, though. You do occasionally see it in games. Of course it's only challenging the first time, after that it's just mildly annoying. When there are only a limited number of people to talk to, and only the important ones have actual names, it also by default narrows down how much you have to search and encourages a brute-force solution of just talking to everyone until the right option pops up, though.
I think one way to make things more challenging is to offer mysteries to solve, though. You do occasionally see it in games. Of course it's only challenging the first time, after that it's just mildly annoying. When there are only a limited number of people to talk to, and only the important ones have actual names, it also by default narrows down how much you have to search and encourages a brute-force solution of just talking to everyone until the right option pops up, though.