This article explores the notion of connoisseurship as a framework for learning about adolescents' lives and literacies and developing relationships in literacy classrooms. Drawing upon data from a two-year qualitative study of the collaborative inquiries of a community of student English teachers, the author examines inquiry projects written for an English methods course in which two student teachers, Alex and Jared, construct counternarratives about the promise of students who had been positioned as problems within their schools. These examples illustrate how becoming connoisseurs of adolescents' distinctiveness and abilities can be a basis for developing counterpractices in literacy classrooms, opening spaces of possibility for otherwise struggling students to begin to reorient their negative trajectories in school. Among other implications, this work suggests the positive consequences of teachers' attentiveness to students' literacy practices, and the importance of teachers cultivating more relational stances toward students.