In this epistolary paper, we draw on the work of an interdisciplinary, psychosocial study of the relationship between time and care, Waiting Times, to explore the significance of a book of letters as a waiting object. Words in Pain, a collection of letters by Olga Jacoby (1874–1913) to her doctor and family written in the shadow of her early death, was published posthumously in 1919 as the nation emerged from World War I and the Great Flu Pandemic; while a new edition was published in 2019 just before the COVID-19 pandemic forced the relationship between waiting, care, vulnerability and interdependence into consciousness. We argue that Jacoby’s passionate reflections on her children and her imminent death show her working out how to live well in the face of a loss that is to come, while using her letters to take care of the future: a future that includes her children and the future generations to whom her letters have come down. We also explore how Jacoby’s first editor in 1919, who published the book anonymously, perhaps to protect the identity of her well-known doctors, and her 2019 editors, who restored Jacoby’s place in time, each performed an act of care, for both the past and the future. The act of writing and reading, but also that of editing, thus provides a container of time and care, while the letter becomes a waiting object that offers to reanimate a relationship to a future into which the writer knows she cannot endure.