How do teachers build an understanding of their relationships with the boys they teach? This article examines an inherent complexity in the teacher-boy relationship that is rooted in a fundamental relational tension: genuine learning requires the development and nurturing of trustworthy relationships, yet many boys are faced with a cultural mandate of separation from relationships, especially care-giving ones such as parents and teachers. One area in which boys’ negotiation of this paradox is visible is in the examination of some boys’ resistances to their teachers, the curriculum of school, and school culture. Through an action research qualitative, relational methodology, this article examines teachers’ understandings of this paradox. Participants were members of a Teaching Boys Study Group, a forum of teachers dedicated to studying teaching, gender and relationship. Findings of this study reveal that when participating teachers confronted boys’ resistances in school, they were engaging a critical intersection of their teaching identities, culture and relationship. Specifically, they confronted a relational paradox that challenged their sense of self as teacher and connections with the boys they taught.