This study applies Relational Dialectic Theory to analyze the stepparent and stepchild relationship of one family. The data is documented in an autoethnography. Autoethnography is an approach to data collection in which the researcher’s own experience is the source of data, and the experience is studied to deepen understandings of social reality. This study highlights the complexity of the stepparent-stepchild relationship, the uncertainty surrounding the stepparent role, and identifies the dialectic tensions that exist within the stepparent-stepchild relationship. The dialectics identified by this study include: emotional-closeness-distance, past-present, autonomy connection, and parent-friend. The findings related to how these dialectic tensions emerge and are managed within stepparent-stepchild relationships have implications for stepparents and spouses of stepparents and for new parents and parents in traditional family structures.