This study explores the phenomenon of dilemma in paediatric practice. Using a hermeneutic phenomenological method informed by the writings of Heidegger [1889-1976] and Gadamer [1900 -2002] this study provides an understanding of the meaning of ‘being in dilemma’ from the perspective of predominantly paediatric health care professionals but also families in New Zealand. Study participants include four families who had a child requiring health care and fifteen health care practitioners from the disciplines of medicine, nursing, physiotherapy, play specialist and occupational therapy who work with families and children requiring health care. Participants’ narratives of their experiences of ‘being in dilemma’ were captured via audio taped interviewing. These stories uncover the everyday realities facing health professionals and families and provide an ontological understanding for the notion of dilemma. The findings of this study suggest that experience of dilemma for health professionals reveals a world that is uncertain and questionable where they are thrown into having to make uncomfortable choices and must live with the painful consequences of their actions. The consequences of being in such dilemma have to find ways of living with the angst, or risk becoming too sensitive or desensitizing. For families the experience of dilemma reveals a similar phenomenon most evident in circumstances where they feel totalized by the impact of heath care encounters. This study has uncovered that the perspectives that health professionals and families bring to the experience of dilemma reveal different concerns and commitments and may be hidden from each other. This thesis proposes that health professionals and families need support in living with their own personal encounters of enduring experiences of dilemma.