The social and educational benefits of cultural exchange within the realm of art are often asserted. However, what of the meaning and value of the actual artworks arising from those exchanges? This paper analyses the barriers to shared understanding that arose in relation to an extended exchange between Japanese and British artists and philosophers on the connection between Nature and Art, 2011-13. First, cultural interfacing is explored in relation to four types– combinatorial, hierarchic, hermeneutic, and thematic – and the case is made that communalities of practice alone cannot guarantee true cultural integration or understanding. Next, six Japanese and Western concepts of ‘Nature’ – as an ontological entity, a class of objects, a domain, a force, a system and an Ideal - are distinguished in relation to the history and beliefs of those cultures. The argument then moves to the interface between Art and Nature: Nature can be the subject of Art, but can it literally be its content? Finally, the relationship between culture and theory is itself explored in relation to two artworks, and their supposed meanings and links. The Appendices include a detailed summary of the distinctions between Japanese and Western aesthetic systems