The importance of imagination in understanding sustainability has often been overlooked. This paper examines acts of imagining in teaching and learning that elicit and enable the emotive experience of empathy. I frame ways of thinking about imagination and empathy through theoretical perspectives of otherness. I report on research findings into the nature of imagination in environmental education contexts in Australia, explored through interviews with educators and participant observation. Analysis pays attention to how teachers and students imagine and empathize in order to more fully understand. The importance of being able to imagine other places, times, and perspectives in environmental education emerged strongly. In this paper I highlight how feeling empathy involves actively imagining the other, and how the relations between self and others can become contiguous through empathic and imaginative ways of understanding.