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Message: <blockquote data-quote="77IM" data-source="post: 6902313" data-attributes="member: 12377">Three words: Piss. Him. Off.If you want players to act emotionally, anger is one of the easiest to trigger. The tricky part is, you don't want him to be angry at you, the DM; you want him angry at an NPC.The whole "quest to eliminate Chaos" immediately popped into my head a Joker-esque character who taunts the PC and mocks his tactical approach. Some chaotic power keeps this guy alive. Ooooh, maybe a Rakshasa or other fiend; when they get killed on the material plane they just come back on their home plane, so he could continue harassing our PC protagonist for quite some time before the final takedown! And if you do it right, then when the PC finally eliminates their NPC rival, it should be very satisfying. Some of the most engaging and memorable role-playing comes from interacting with a villain that is "fun to hate."Again, be careful not to overdo it and make the player actually be angry with you. Try to create an NPC that offends the PC's sensibilities somehow, but doesn't actually "harm" them in any way. Like, destroying all the PC's magic items will make the player angry, which is not what you want. You know your players better than I, so it's up to you to know which buttons to push. (Or not push -- if your player is very sensitive, maybe this whole approach is a bad idea.)</blockquote>