The research reported in this article intends to contribute to an understanding of how out-of-school literacies can influence the present and future learning of adolescents. Evidence suggests that students, boys particularly, are becoming literate in many ways through out-of-school activities (e.g., video games, Internet browsing, chatrooms), but girls are not engaging in these activities or using them in the same ways. Although girls appear more successful throughout school, the literacy skills they learn may not provide sustained opportunities for acquisition of productive lifelong skills. Neither the negative newspaper reports regarding boys' literacy skills, nor the higher test scores reported for girls, provide the whole literacy and learning picture. Gender-based expectations of teachers, parents, and administrators offer qualitatively different opportunities for boys and for girls that can maintain gender inequities in education. Such expectations can either increase or decrease the opportunities that students, both male and female, are afforded to prepare themselves for today's world. (Contains 2 tables.)