Can genuine love be commanded? This paradox lies at the heart of Deuteronomy 6:5, where God orders humans to love Him - a directive that seems to contradict the very nature of love as spontaneous and freely given. Through analysis of biblical scholarship, psychoanalytic theory, and modern Jewish philosophy, multiple interpretations emerge to resolve this theological tension. William Moran's ancient Near Eastern covenant analysis reframes "love" as loyalty rather than emotion, while psychoanalysts Theodor Reik and Erich Fromm view divine love through the lens of ego-ideals and overcoming separateness through action. Among philosophical perspectives, Hermann Cohen interprets the commandment as an act of will and knowledge, Martin Buber sees it as an invitation to authentic I-Thou relationship, and Abraham Joshua Heschel reconceptualizes it as God's plea reflecting divine pathos. Franz Rosenzweig offers the most compelling resolution, presenting the commandment not as coercive demand but as God's signal of trustworthiness that enables human reciprocal love. These varied approaches suggest the apparent contradiction dissolves when the divine command is understood as invitation, enablement of trust, or expression of divine vulnerability seeking human response.