Using a feminist postmodern perspective and the sensitizing concept of split loyalties from Contextual Theory, the primary purpose of this qualitative study was to develop a better understanding of how adult female adoptees from closed adoptions negotiate relationships with their adoptive and biological mothers post-reunion. We conducted semi-structured individual interviews with nine adult female adoptees, ages 28–52, who were adopted prior to the age of two. Six were Caucasian, three were African American, and the average age at reunion was 29. Grounded theory techniques were used to code the qualitative data, in particular the constant comparative method of analysis. Four main categories emerged: (a) Negotiating Mother–Daughter Relationships, (b) Relating to Mothers Equitably, (c) Loyalty, and (d) Adoptees’ Emotional Needs. Our findings suggest the adoptive mother–daughter relationship has a salient effect on adoptees’ relationships with biological mothers post-reunion. Loyalty to the adoptive mother seems to influence the evolving relationship and closeness displayed toward the birth mother. Adult female adoptees from closed adoptions described struggling with managing their two mother–daughter relationships and need clinical help addressing their own emotional needs.