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The aim of this research is to explore collaborative AI systems to promote healthy lifestyle changes. With a focus onolder adults, a participatory design process was initiated, involving a team of researchers in occupational therapywith expertise in engagement in meaningful activities such as among older adults, human-agent interaction,and artificial intelligence. The scenario of collaboratively assessing past activities and planning activities of thecoming week - between the human and AI agent -guided the development of a novel, person-tailored storytellingsystem, based on argumentation theory. A framework was developed, integrating semantic user models, dialoguetypes, and structured argumentation to guide personalised story generation towards motivational and reflectivegoals. The formative evaluation highlighted critical challenges, including narrative inconsistency and hallucinatedcontent, motivating the future inclusion of reflective AI components. This work contributes to the methodologicalfoundations of designing trustworthy, purpose-driven storytelling systems that can be extended for futureHuman-AI collaboration.