This study examined the reflections of gender nonconforming men on their lived-experiences as boys in the heteronormative environment of high schools. Participants self-selected for the study based on their perceptions of being othered as boys in high school due to their nonconforming expression of gender. The study targeted men who had graduated with a Manitoba High School Diploma within the last 5 years. The methodology of this study was underpinned by an interpretivist theoretical perspective. The purpose of the research and the positioning of the researcher were influenced by the socially critical research paradigm. Narrative methods were utilized for the reporting; the lived experiences of the participants while in high school. The study found that high schools continue to be heteronormative environments that present difficulties for gender nonconforming boys. Although participants felt that the situation in high schools may be improving, all felt that much more can, and should, be done to improve conditions for gender nonconforming youth. Findings suggest that policy and practice at the school, district, and provincial levels need to be examined and, where necessary, changed to address the treatment of gender nonconforming boys in high schools.