It is increasingly accepted in the psychoanalytic world that an essential pathway toward change is in the development of an intimate relationship and, as with all intimacies, each participant influences the other. In this presentation I describe an extremely long analysis in the context of how our mutual development and evolution have had synergistic and beneficial effects. I will use this case material to elucidate my ideas about the tension between desires for progress and anxieties over change. We all know that trauma has pernicious effects. In that regard I will describe how trauma profoundly affects crucial separation-individuation dynamics and contributes to difficulties in finding new and more satisfactory solutions to internal conflicts. Self-defeating and masochistic needs deriving from perceived guilt often predominate in such cases, and I will describe their prominence in Maggie’s dynamics.