In the West, chaos is typically linked with order, from the Genesis story, through our psychological fictions, to contemporary theories of chaos in the physical sciences. The intention of this dissertation is to show that chaos is to be viewed rather as the guardian and the intimate companion of eros and not the matrix out of which order is created. When chaos and eros are twinned in this fashion, they challenge our reigning paradigms of control and domination over the world. This hermeneutic study attempts to illustrate how from the point of view of the archetypal field of soul and its mythologies, chaos linked with eros invites us into the epiphanies of love and its shadows, invites us into reverie on the mysteries of, and obstacles to, our loving and being loved. Such a coupling resituates us within the larger fabric of creation. Love is first and foremost a cosmic mystery that fuels the integrity of the universe. All of us in one way or another struggle with love, or suffer its absence. This & ldquo;difficult work, & rdquo; as Rilke (1954) calls love (p. 54), is often the orienting star of analytic work, and arguably the one experience we would rather not leave this life without having known. This study addresses suffering as a shadow of love through the image of the Orphan, and chaos as that Other that links with the marginalised feminine and especially women's experience in Western traditions. In my reflections and examples, I try to show that our attempts to become more conscious continue to remain inadequate unless resituated within a devotion to the complexities and refinements of love and its shadows. This task is perhaps one of the most demanding and difficult of all human efforts. A key point in this thesis is to show that in our contemporary world, chaos is a vocation, calling us into the unus mundus, into a world of synchronicities where the desire of spirit for matter is witnessed. Here new syntheses emerge that resituate human life as merely one expression of a divinely created cosmo-psychic realm that glistens and ripples with life both subtle and manifest. This work is linked intentionally and soulfully to theoria in its original sense as a contemplation, and to the hermetic tradition as that school in the early centuries of the first millennium AD that valued immediate experience as a source of revelatory gnosis, as much as book learning. Depth psychology is perhaps the contemporary emergence of these ancient streams. Thus in my dissertation what is important is the style of writing as much as the content. Hence the format is a blend of experiences and reflections including dream, vision, and clinical material.