Robert Grossmark expands our current understanding of the relationship between hermeneutic psychoanalysis, relational psychoanalysis, and complexity theory, illustrating this relationship in the context of presenting his work and discussion of his group psychotherapy experiences. Complexity theory continues to be increasingly elaborated in psychoanalysis and integrated into psychoanalytic theories centered on multiplicity, dissociation, and enactment. The utility, vicissitudes, and potential problems with this integration necessitate an emphasis on the distinction between thinking phenomenologically and thinking explanatorily. Recommendations are offered for a more seamless integration and application of these theories.