This article explores the impact of the analyst’s life-threatening illness on the analytic couple; it is informed through two theoretical lenses - Freud’s ideas about the vicissitudes of mourning, which have been elaborated on by Melanie Klein and John Steiner, and Christopher Bollas’s ideas about destiny and idiom. Clinical material will focus on my on-going work with a middle-aged man who has a history of early abandonment and loss and who struggles with being able to remain separate from his objects while being in relationship with them.