The world’s first legal euthanasia death occurred in the Australian City of Darwin on Sunday 22 September 1996 when Bob Dent ended his life under the Northern Territory’s short-lived Rights of the Terminally Ill Act 1995. Dent’s death intensified argument about euthanasia in Australia, transforming the debate from a textbook discussion in social ethics into a vigorous and divisive social dispute. The day before he ended his life, Dent dictated a letter, written down by his wife. This description of his experience with terminal illness is graphic—the letter, his last effort to bring the plight of those living with terminal illness to public consciousness. In this paper I outline issues from the perspective of those, who like Bob Dent, the choice to die with dignity is personal and urgent. Rather than approach the issue purely from the theoretical, academic debate therefore, I present aspects that are largely unknown unless the experience of life-denying symptoms becomes real. From these aspects, dilemmas and consequences emerge that are not framed through the academic debate and in this way, I argue for the possibility of a framework that could change the law.