Those who teach, or intend to teach, young children undergo careful scrutiny as to their suitability for the role of teacher. In general, professional monitoring of teaching standards and teacher qualities are reasonable expectations. However, a set of related cultural practices embedded in such monitoring purposefully and unjustly impact men who wish to teach young children. The underlying issues of this injustice are: (a) social expectations for female and male teachers when teaching is construed as caring; (b) the inferred sexual orientations for suitable and unsuitable teachers; and (c) the accusation of pedophilia used as a gatekeeper. Yet these socially constructed categories and their interrelationships are sufficiently ambiguous that each has been deployed in the extortion of male teachers. This article examines the dynamics of unreasonable monitoring of male teachers who either teach or want to teach young children.