An increasing number of children are expressing themselves in gender-expansive or gender-variant ways. A subgroup of those children are girlyboys: boys who accept themselves as boys but cross culturally defined gender lines in their attitudes, behaviors, and desires. Using clinical material, written accounts, and personal observations, this paper investigates the experience of parents raising these boys. Facilitative parenting is differentiated from obstructive parenting within the rubric that gender-fluid outcome is healthy and parents can have influence in this arena. The experience of parents with their girlyboys is also offered as a window through which to view a young boy's protogay development. Analysis is made of the ways in which the psychoanalytic lens has traditionally blurred or distorted our thinking about parents' roles in gender-variant children's development. An alternative view of parenting, informed by the work of post-modern psychoanalytic gender theorists, is proffered, with an end to reinforcing healthy gender-fluid development.