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Attachment theory described by John Bowlby greatly influenced the perception of relationships. The theory proposes a framework for thinking about relationships—the propensity of mankind to seek closeness to particular others. Attachment behaviour and the longing for a secure base are focal points within the concept of attachment. Both are thought to play a role from cradle to grave. In palliative care (with approaching death as the ultimate threat to connection) dynamics in relationships will inevitably change. This article introduces the concept of “the palliative paradox”, a perspective on dynamics within the relational realm. It provides a framework for clinical thinking and points to possible interventions. It can also be used as a means of psycho-education for patients and family. As such “the palliative paradox” can provide insight for clinicians, patients, and family alike. This enables all involved into becoming and being a secure base for each other. The presence of a secure base amidst the process of separation makes it possible to die connected. Thereby increasing the quality of life, the focal point of palliative care.