In this paper, I will reflect on advance health care directives, from a bioethical point of view. Advance health care directives, which deal with the right of self-determination, are now regulated by the Italian statute no. 219/2017. I will deepen the concept of rationality and capacity for rational choice in advance decisions, by looking at the figure of Ulysses, who is considered to give his companions the first living will in Western history. From Homer and his “dilemmatic rationalityµ to Ion Elster and his “imperfect rationalityµ, and return, this path will give the opportunity to consider advance health care directives as instruments of a dialogical-dialectical resolution of dilemmatic situations.