Although interdisciplinary scholars have long debated the ethics of empathy, it continues to be widely seen as universal, prosocial, and reparative in education. Subject English, long associated with the work of producing civilised, moral and cultured students, is a critical locus for the activation of empathy. But what becomes of empathy in the high stakes senior secondary English classroom? Drawing on an in-school ethnography, the paper begins to map the ways in which empathy is activated through and around set literary texts in Victorian Certificate of Education (VCE) English classrooms in Australia. In so doing, it highlights the unpredictable nature of empathy as a relation exceeding pedagogical mediation, as well as the troublesome aspects of empathy entangled with neoliberal imperatives and the interpellation of the civilised English student. Finally, it turns to the generative possibilities of an empathy unsettled -- an unruly empathy.