This paper explores the factors that may influence the social and relational development of empathy in a Year 13 classroom from a kaupapa Maori perspective, and discusses how these factors compare with a Western perspective of empathy. Understandings of empathy are widely documented in the conventional literature and, while the realities pertaining to empathy have been part of the fabric of Te Ao Maori (the Maori World), there has not been satisfactory levels of understanding by Western social scientists. It is proposed in this study that viewing empathy, through a bicultural lens, may provide relevant and meaningful understandings of empathy for both partners to the 1840 Treaty of Waitangi. This study explores the heuristic understandings of how the research participants experienced culturally-sensitive understandings of empathy within their face-to-face classroom interactions. The understandings of 14 students and their teacher were analysed through the Maori concepts of manaakitanga, kotahitanga, rangatiratanga, whanaungatanga and pumanawatanga; constructs that underpin Macfarlane's (2004) Educultural Wheel. Adopting a qualitative case study methodology, the participants engaged in an iterative dialogical research strategy based on Gadamer's hermeneutics (1975, 2001). This iterative research strategy enabled the students and their teacher to co-construct their developing understandings with the researcher, over time. Data collection occurred over a six-month period and comprised: 14 initial one-on-one interviews with students and the teacher; one student focus-group interview, and individual respondent-validation interviews with, respectively, 12 students and one teacher. Classroom participant observations, students' written diaries and researcher field notes enriched the interview data. Factors identified by the research participants affecting the development of empathy from kaupapa Maori perspectives are presented, and the relation to Western perspectives are discussed. The findings indicate the importance of social engagements that are founded on an ethic-of-care (manaakitanga) and are duly focused on taking an interest in the individual. The findings of the study may be helpful in informing the development of more equitable and culturally-responsive educational practices (Castagno & Brayboy, 2008).