Psychoanalysis is inherently messy and mysterious. The mysteries of the psychoanalytic process are viewed through the lens of chaos and complexity theory. The analyst-analysand relationship is an example of a nonlinear dynamic system, meaning that it is continuously changing, adapting and coevolving; deterministic predictability is lost in the process of continuous adaptation. The fractal nature of the psychoanalytic relationship and the emerging qualities that arise from its self-organizing system and from bottom-up therapeutic approaches are explored and examined in relationship to the nature of healing. The analyst must tolerate chaos, uncertainty, and messiness for the healing process to naturally emerge. In addition, the age-old question of free will versus determinism is examined from the perspective of complexity theory.