We examine the literacy gender gap through the documented experiences of 3 representative high schools boys and their teacher--how they view themselves as students, their dispositions toward schooling and education, and their engagement with literacy--as a way to further understand how literacy teachers can better work with them. We offer a case study analysis of the boys' struggles with academic reading in high school reading classes aimed at addressing the needs of young people who read far below grade level in school. We highlight the multifaceted, complex nature of "struggle" or "reluctance" toward academic reading and argue that no 1 single factor drives or maintains reluctance. Instead, we demonstrate how cycles of narrow definitions of literacy and what it means to be literate, negative experiences with teachers, frustration with academic and social structures in schools, and difficult relationships at home all work together to perpetuate struggles with reading.