Hermeneutics is both a philosophical tradition and a methodological resource. In this qualitative study, hermeneutics provided, simultaneously, a framework and a methodology for understanding empathy in synchronous multimedia conferencing. As a framework for the design of the study, hermeneutics supported the overriding objective to understand the human phenomenon of empathy and students' and teachers' experiences of this phenomenon. As a methodological resource, hermeneutics pointed to an approach to data collection and analysis that would allow us to honour and remain faithful to participants' stories of their experiences of empathy in on-line educational environments. In this article, we provide an explanation of the iterative approach used to interpret empathy within classroom environments devoid of face-to-face interactions. Those approaches offered increasingly deeper understandings of the ways in which people are able to perceive how others "feel" in on-line environments.