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The purpose of this article is to encourage reflection about children and adolescents who are expanding gender expression in this contemporary cultural moment. More specifically, to consider how relational rupture and its affective counterpart, grief, may become encrypted in gender. Attachment theory’s articulation of the intricacies of loss, in combination with psychoanalytic and systems theories, will serve to parse out the complex and paradoxical communications within this potentiality. Toward this end, my clinical process with five gender nonconforming children and adolescents will be discussed. The clinical section forms a tapestry weaving between similarities and differences in the expression of gender within the fabric of an attachment relationship. To link the clinical process to a larger cultural discourse, this article brings literary voices into the conversation, including Carson McCullers’s in Member of the Wedding and Jennifer Boylan’s memoirs of life in two genders and other writings. These sources crisscross/queer developmental time lines, disciplinary mediums, culture, and family dynamics to open up an inclusive conversation about gender subjectivity. The therapeutic process, with particular emphasis on the importance of play, is linked to advances in developmental science. Thinking with the children who vary the expression of gender can potentially inform our conceptualization of gender development, more generally.