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This article illustrates analytically oriented psychotherapy with the homeless. The concept “Difficulty to Reside” is introduced to describe the inherent emotional difficulty of many homeless people to tolerate the idea of a home as well as an actual physical residence. This is not only the difficulty of bearing a home in the physical sense, but the difficulty of being within the envelope of a close relationship, and even a failure of the individual to be close to themself. Three layers of the difficulty to reside are noted, by means of clinical examples: the autistic-schizoid layer, the psychotic layer, and the layer of trauma, personality disorders and substance abuse. Modes of intervention are suggested. The therapist’s mind as a metaphorical home for the patient is illustrated. The emotional dynamics of treating the homeless are analogized to Calvino’s “Invisible Cities,” as alternation between destruction and construction. The homelessness in the therapist’s psyche is emphasized. Finally, the metaphor of “the Edge of Chaos Theory” (physics/biology) is presented as an area of encounter between homeless patient and therapist.