This chapter explores the concept of boyhood and examines the challenges of negotiating identity in a digital age saturated with conflicting messages. It also considers how shifting perspectives on women and girls have reshaped the context in which young men and boys navigate masculinity. Masculinity is unpacked as a complex construct influenced by class, race, ethnicity, education and demographic factors. The chapter addresses the impact of pornography, often negotiated in isolation, alongside the pervasive influence of social media and online gaming. These rapidly evolving digital spaces are scrutinised to reveal their role in shaping contemporary masculinities.