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Parenting gender variant children presents challenges both to parents’ internal development and to their tasks of parenting. Although there is a burgeoning literature on many topics regarding transgender development and experience, there is little that directly addresses parents’ internal emotional experience of their child’s gender variance. In this article, parent development and parenting tasks particularly relevant to parenting children with “differences” are reviewed, along with Diane Ehrensaft’s delineation of parent experience with gender variant youth. Next, assumptions and biases are considered. Then, as the central focus, I describe and discuss my own journey with a gender variant child, augmented by the experiences of others.