Digital media’s growing influence on children during their critical developmental years affects youth of all gender identities. In this “Ask the Experts” webinar, the impacts of these online interactions on the identities and experiences specific to boys in their journey to “manhood” is examined by a panel of experts, researchers, and health practitioners. Impacts of technology and digital media on risk-taking behavior, body image, self-esteem, and perceptions of gendered norms is discussed, as well as tips for parents to help their child maintain a healthy relationship with digital and social media influences.