Focus of Study: This article investigates how teachers' relationships with boys can be central in bolstering boys' resilience and connection to their work in schools. Specifically, we examine how teachers understand the ways that their relationships with boys shape their teaching practice as well as their understandings of boys' learning in school. As school violence perpetrated by boys continues to make the headlines, and as many boys' achievement continues to lag behind that of girls, especially boys of color and boys in the lower socio-economic classes, we must engage the question of whether and how teachers come to know the boys they teach. Context: Recently, boys' development and performance in school has taken center stage in educational research on gender and schooling. Building on a significant history of research on classroom relationships as well as current findings that reveal the centrality of relationships in children's learning, this article seeks to investigate the ways that socio-cultural forces of gender both shape teachers' conceptions of relationships with boys as well as teachers' capacity to connect with the boys they teach. Methodology: In order to examine the prevailing research questions, a Teaching Boys Study Group was formed, comprised of thirteen pre-K-12 teachers. Teachers presented detailed descriptions of individual boys to each other and then examined questions of pedagogy, gender and identity. The data was analyzed using a qualitative voice-centered relational method that required multiple listenings or readings of the data in order to surface the central tensions that the teachers confronted when considering their relationships with the boys they teach. Findings: Our findings revealed two central tensions that teachers confront when considering the intersection of gender and the relational context of teaching and learning. The first tension encompasses teachers' efforts to locate, appreciate and preserve boys' individuality while at the same time confronting the pressures that teachers face to act as forces of enculturation. The second tension focuses on the complexity involved in locating teachers' teaching identities--especially the ways that gender shapes their teaching identities--while at the same time identifying the meanings that boyhood holds for their male students. This tension became particularly acute when examining issues of boys' resistance to school and to teachers. Conclusions: These findings suggest that the ways teachers come into relationships with boys shape and is shaped by the teachers' identity, the extent to which the boys express resistance to the school and classroom culture, and the forces of the school culture on both the teacher and the boy. When teachers can become aware of these forces, they have the capacity to investigate their own life histories, seek insight and support from colleagues, and revisit and hone their practice. Such awareness allows teachers to enter into relationship with the boys they teach, resist the forces of relational disconnection, and ultimately support their students' learning. The findings suggest the essential need for and careful planning of professional development contexts that can support teachers' inquiry into issues of gender, identity, teaching and learning.