There is an urgent global need to promote healthier and more sustainable eating habits. Yet digital applications in this domain often disregard the complex array of factors that shape food perceptions and practices, leading to exclusion and disengagement. At the same time, AI offers opportunities to adapt digital systems based on individual preferences and behaviours. This paper reports the first stage of work to design an AI-powered digital tool that introduces users to principles of healthy and sustainable eating across different cultural contexts. Using cultural probes and semi-structured interviews, we investigate lived experiences and socio-cultural connections to food and eating practices. Our findings reveal the diversity of eating frameworks and highlight the need for adaptive AI technologies that can support tacit knowledge and accommodate varying understandings of health and sustainability. We contribute to advancing inclusive and culturally resonant AI design, with the potential to increase the engagement and impact of digital tools promoting dietary change.