Research into homelessness has been predominantly quantitative in design, solution-focused and may have effectively concealed the phenomenon itself. This study utilised a hermeneutic phenomenological methodology, based on Martin Heidegger’s philosophy, to reveal some essential, constitutive characteristics of homelessness. In-depth qualitative interviews were conducted with six participants accessed through a service provider for homeless persons. Passing Time and Taking Care emerged as essential, constitutive characteristics and were examined to deepen our understanding of the meaning and ground of homelessness itself (Heidegger, 1962). Passing Time revealed boredom as the mood of homelessness and disclosed the daily challenges faced in filling or wasting time when homeless. It is revealed that through profound boredom, homeless persons exist as an empty self, suspended in an empty world. Taking Care disclosed something of the participants’ capacity to take care of themselves and to access care from others. It revealed something of their relationships with self and others and the anxiety such relationships evoke. Homeless persons struggle profoundly to access emotional containment either internally or externally. They exist in a state of deep anxiety and internal turmoil in a rejecting, excluding world. It is recommended that government agencies and homeless services adopt more inclusive, creative, caring attitudes and policies underpinned by an understanding of the homeless persons need for containment in order to become a more integrated and cohesive self. Finally, it is recommended that psychotherapists are actively involved in the design and implementation of programmes to collaboratively work with homeless persons towards re-integration into mainstream society.