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This study uses generative AI to investigate the influence of building façade geometry on human physiological and psychological health. Employing Christopher Alexander’s fifteen fundamental properties of living geometry and ten emotional descriptors in separate tests, ChatGPT evaluates simple, contrasting window designs. AI analyses strongly and consistently prefer traditional window geometries, characterized by symmetrical arrangements and coherent visual structure, over fragmented or minimalist-modernist alternatives. These results suggest human cognitive-emotional responses to architectural forms are hardwired through evolution, privileging specific geometric patterns. The findings challenge contemporary architectural preferences and standard window archetypes by emphasizing the significance of empathetic and health-promoting façade designs. This novel use of AI suggests integrating neurodesign principles into architectural education and practice to prioritize urban vitality through psychological well-being.