This chapter examines sex, intimacy and privacy. It foregrounds the young men’s concerns about the accessibility and consumption of online pornography in relation to its ubiquity and infiltration in their everyday online experiences. They present an overwhelmingly negative picture of how online pornography impacts on their lives including struggles with addiction, desensitisation towards explicit content, distorted views of sex and sexual consent, the objectification of women’s bodies and the degradation of their relationships with girls and women. The chapter also foregrounds the young men’s concerns about privacy and safety online, noting issues ranging from online scams targeting family members to personal encounters with catfishing. The discussions around the regulation and censorship of online content highlight the struggle these young men experience in striking a balance between user protection and freedom of expression. The chapter includes analytic summaries to draw attention to curatorial intentionality, scepticism, ethical engagement and reflexivity [Pangrazio, L. (2018). Young people’s literacies in the digital age: Continuities, conflicts and contradictions. Routledge].