This essay examines the concepts of freedom and free will within the context of an intersubjective systems theory perspective of psychotherapy. While free will and freedom remain a basic challenge throughout human life, they are both conceptualized as emergent properties of early childhood development within its socio-cultural-historical context. If an authentic experience of selfhood is seen as an endangerment to attachment a conflict may ensue between integrity and the bond which impedes the ability to tolerate ambivalence. Ambivalence, however, allows choice, and choice is the essence of free will and freedom. In psychotherapy these issues will be embedded in the life themes of both participants and will emerge as collisions and collusions in the psychotherapeutic interaction. Change will therefore occur as an emergent product and property of the relational system created by each therapeutic dyad and its ability to therapeutically work through these fundamental issues. Two clinical examples are provided.