With longer life, many people reach ages that were rarely achieved even a generation ago. But psychology and psychoanalysis have not fully engaged with the travails of old age. This article describes the difficulties many couples and individuals have facing the loss of physical and mental health in old age. By examining three clinical cases, it explores the difficulties couples have facing their inevitable losses, the particular difficulties for a couple when one partner has dementia, and the pain of an elderly patient facing the inevitability of her own death whilst full of regret for a compromised marriage and loss of opportunities in her life. The article describes how psychotherapy for couples and individuals lessens the sense of being alone and inscribes a sense of “being accompanied” externally and internally that soothes the pain of loss.