For this study of sexual education in Israeli Modern Orthodox high schools, we interviewed teachers at the crossroads of conflicting values. Caught between a commitment to promote traditional practices and values, and a sense of obligation to serve as caregivers to students whose lived realities often do not fit neatly within the framework of religious norms, these teachers experienced acute confusion regarding their roles and even identities as educators. This confusion expressed itself in teachers' inner doubts and played out in actual teaching practices. These practices took two primary forms. The first, comprised of extremely oblique forms of sexuality education in the classroom, was regarded by most teachers as problematic and ultimately ineffectual. It did not permit them to fulfill their sense of obligation as caregivers. Thus, an additional private discourse emerged outside of the classroom with its own set of rules and motifs. This discourse took the form of sexual absolution and confession. While allowing teachers to act as caregivers, and possibly providing some benefit to students as well, this practice, we discovered, was very far removed from the teaching of sexuality education.