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Accounts of the experiences of gender variant individuals that have recently received attention in the popular and psychoanalytic literature have led to an increased appreciation for the complex nature of identity; gender development; and the interaction of mind, body, and the social environment. Although there is still a great deal to be learned about the developmental trajectories of transgender identities that fall within what is a more familiar, male/female binary-based landscape, even less is known about developmental pathways for individuals whose gender identities remain neither comfortably male nor female. In this article, we present selected episodes reflecting our experiences as a family, drawn from over a 25-year period in which a gender variant individual, along with the rest of us, grew up. We tell this story—our family’s story—to better understand what we have been through and learned, to help other families going through similar experiences, and as a thought-piece to clinicians and students of gender. The result is both a narrative and a meditation on the nature of gender identity and gender development.