Artificial Intelligence (AI) can provide novel insight into how complex lifeforms will evolve. Investigating the hypothesis that this evolution will follow the 15 fundamental properties listed in Christopher Alexander’s Nature of Order , this art project recruits AI to impersonate Socrates and domain experts to probe refutational and constructive elements as a means of facilitating meaningful discourse. The fictional dialogues and their core outcomes are transferred into AI generative visual representations. The project concludes with a synthesis of the insights gained from the exploration, providing a narrative about the Nature of Order as a vision of augmented wisdom.