This chapter examines Paul Tillich’s interpretation of tragedy in relation to love and courage. Tillich rejects both optimistic illusions and nihilistic despair, situating tragedy at the heart of human existence. Love, for Tillich, is not sentimental harmony but the power that unites what is separated, always vulnerable to distortion and failure. Courage, correspondingly, is not the absence of fear but the strength to affirm life in the face of anxiety, guilt, and non-being. By integrating tragic awareness into his theology, Tillich demonstrates how love and courage sustain existence without denying finitude. The chapter highlights Tillich’s engagement with existentialist themes, particularly his dialogue with Nietzsche and Kierkegaard, showing how tragedy informs his critique of modernity and his rethinking of faith. Rather than resolving tragedy, Tillich transforms it into a theological resource that discloses the depth of human vulnerability while affirming the possibility of renewal through love’s unifying power.