The disruptive advancement of artificial intelligence (AI) has triggered profound transformations, confronting education with the formidable challenges and innovative opportunities of human-machine collaboration and cross-domain integration. As dialogue constitutes the core vehicle for human cognitive advancement and civilizational transmission, it has been endowed with new connotations and values in the intelligent era. This paper designed a unique format of dialogue among three generations of scholars (a senior educational scholar, a university teacher, and a graduate student) in conversation with AI. Through a typical case of AI-empowered academic inquiry at overseas universities and situated within the context of educational development in the Hainan Free Trade Port, the paper constructed pluralistic dialogue scenarios interweaving history and reality, humanities and technology, and the virtual and the real. Focusing on the new forms of human-machine collaborative dialogue, the paper ranged from interdisciplinary reflection on the social history of AI to the innovative integration of Hainan’s local culture with AI education, and discussed the new perspectives on teacher education and the new spatial-temporal possibilities for education innovation in the intelligent era, offering both theoretical exploration and practical inspiration for revitalizing tradition and embracing the future.