Some questions are perennial, forever reemerging in textbooks when the debate is highly abstract but occasionally changing history when someone acts dramatically on conviction. Think of Socrates asking “What can we know?” and being willing to drink the hemlock, or of Jesus asking “Who should we love?” and being willing to stretch his body on a cross. A third enduring question - “Are we meaningfully free?” - is the chief focus of this essay. I do not expect to settle the ancient debate about freedom of the will, but I do hope to situate it theologically by critically examining Søren Kierkegaard's views in light of some significant precursors. Kierkegaard worries about how to balance the contingency and fallibility of human deliberation and choice with the indispensability and reliability of divine providence, but he does not treat these matters abstractly or in isolation. He is too Socratic for mere abstraction about human freedom; indeed, his fully Christian understanding is highly dramatic (even paradoxical) at times, in an effort to be true to lived complexity.