This article examines the complex, deeply personal processes that elementary educators engage as they learn to become inclusive practitioners of gender and sexual diversity (GSD). We complicate literature that highlights structural barriers and negative influences such as lack of administrative support and homophobic attitudes as key factors that constrain educators' willingness and ability to enact inclusive praxis. We argue that preparing educators to affirm GSD demands exploration not only of structural barriers that might get in the way, but also of the emotional and intellectual dimensions of educators' processes of negotiating commitments to GSD-affirming pedagogy and practice. To illustrate the nature of these dimensions, we highlight snapshots of two elementary teachers' processes of grappling with fear, hesitation, and discomfort as they moved toward taking inclusive action in their classrooms. We conclude with implications and recommendations for educators seeking to affirm GSD in their own local contexts.