This study stems from a yearlong qualitative inquiry examining the influence that gender ideologies exercised in the lives of four young men in the high school setting. Utilizing a feminist, post-structuralist perspective (Davies, 1997, 1989; Connell, 1996, 1997, 1989; Martino, 1995), it analyzes how masculinity constructs itself through discursive practices. The study involves four adolescent boys, Michael, Peter, Aiden and Jack, all friends and classmates in a small, Midwestern high school comprised mainly of working class and farming families. This study examines each boy's idiosyncratic positioning within dominant discourses of masculinity, specifically questioning its ability to shape, influence and possibly constrain posture and performance in the classroom setting.