Two six-year-old girls, inhibited socially and constrained in their physical life, were successfully analyzed before and after the effects of the 1970’s Woman’s Movement and Title IX took hold. Surprisingly, despite the significant changes in society from one era to another, both children were unhappy with their identified genders in comparison to boys and they both identified gender as the root cause of their unhappiness. Both children began their treatment with scenarios designed to communicate their concerns, discover what analysis was about, and in particular, assess who I was and who I could be. In the transference-countertransference enactments, they reexperienced the anguish that had traced their downward spiral toward despair. Fathers who were perceived as critical, menacing, and uncaring were held responsible for the misgivings about gender and desire that confounded their children and damaged their self-esteem. Transformations for both children were reflected in the new paradigms they discovered and created within the real relationship with a safe and caring man.