Chlorophilia, a human’s love or attraction to trees and plants (van Biesen), promises an alternative poetic encounter with nature that provokes the question: Can art mediated experiences influence concern and care for flora and the environment? Drawing upon art projects—including Melbourne City Council’s Urban Forest Visual Map (2013) in which people emailed individual trees—I examine how exchanges between humans and plants, mediated by art, can result in emergent states that escape the bounds of the predictable. Focussing on practice within an eco-social paradigm, this paper is historically contextualized by Agnes Denes’ and Katie Paterson’s art projects, where cultivation and growth stands as an essential action. Furthermore, my own projects in Moonee Valley, Craigieburn and Melbourne offer insights into this enquiry via direct observation, reflexivity and practice-based research. I argue that encouraging an engagement with nature via haptic and ocular modes of art practice may facilitate a deeper engagement with, and/or increased appreciation for, flora. Creating circumstances within both gallery and public contexts to engage people with plants, as real and imaginary propositions, offers community members of all ages a mediated pathway into participation and conversation. I speculate that these encounters may assist in establishing connections and creating multispecies relationships in both the short and long term.