Traditional concepts of Christian prayer were difficult to sustain in the wake of the Enlightenment. Kant and Hegel viewed prayer with skepticism, associating it with a pre-modern, magical worldview increasingly at odds with enlightened rationality and emerging scientific paradigms. In this context, Friedrich Schleiermacher and Søren Kierkegaard sought to rehabilitate prayer, relocating it as a technology of the self that was grounded not in magical causality but in existential depth. For both thinkers, prayer emerges at the far edge of human understanding and action, often in situations of distress and anxiety. This paper explores how Schleiermacher and Kierkegaard reimagine prayer within the conditions of modernity, emphasising the inescapable realities of human limitation and uncertainty before the transcendent being of God. For Schleiermacher, petitionary prayer functions as a necessary, though limited, human expression of anxiety and dislocation. The end of petition is to give way to thanksgiving and acceptance, a recognition of human finitude and of the divine as the sustaining ground of being. Similarly, Kierkegaard situates prayer in the context of existential anxiety, portraying it as an act of surrender at the precipice of despair. For Kierkegaard, prayer is not an escape from uncertainty but a transformative engagement with it that fosters authentic selfhood. By analyzing both their distinctive contributions, the paper argues that Schleiermacher and Kierkegaard came to see prayer not as an attempt to control or explain the divine but as a practice of receptivity, faith, and repentance.