This chapter analyses how modern Jewish thinkers and writers pay attention to the more uncomfortable or darker aspects of our life which tend to get ignored in the redemptive narratives with which we are familiar from Christian and, in its secular form, humanist philosophies. Perfection here gives way to frailty, progress to the potential of regression – or in Freud's famous psychoanalytical case studies, repression – and light to darkness. Franz Rosenzweig, one of the most important modern Jewish thinkers, famously understood his Jewishness, as his "dark drive". Ageing is a dark topic, because it involves a deterioration of our health and our capacities. Modern Jewish writing and thought pays attention to dark topics which traditional humanist and Christian philosophies tend to marginalize or neglect.