Gender-transformative approaches (i.e., approaches that support male-identified individuals to critique and resist stereotypical male gender role norms that negatively affect health and well-being) are increasingly recognized as a key health promotion strategy. However, there is limited evidence to date on gender-transformative interventions for male-identified adolescents. In addition, given the dynamic and socially constructed nature of gender, methods beyond quantitative data collection are needed to gain a holistic understanding of promising gender-transformative health promotion approaches. One newer method to capture lived experiences with adolescents is photo-based evaluation, where youth program participants take pictures to represent their knowledge, attitudes, and/or behaviors before and after a program. The present study presents findings from the photo-based evaluation of a gender-transformative health promotion program called WiseGuyz. WiseGuyz is offered to mid-adolescent, male-identified youth in school and community settings, and is designed to promote mental and sexual health and prevent violence. Six youth photographers from a rural Canadian setting took part in this evaluation, taking photos to represent what being a guy in their world meant before and after WiseGuyz. Youth then participated in an individual visual storytelling interview and a group-based photovoice process. Key themes in relation to masculinities that emerged from these data were around changes to (1) social norms and (2) emotionality following program participation, and the need for a safe program space to support these changes. This study adds to literature demonstrating the promise of gender-transformative approaches with adolescents, with implications for future health promotion research and practice with male-identified youth.