This chapter examines the tensions involved in young men’s navigation of leisure, work and identity online. It explores how young men derive pleasure from the entertainment, social connection and professional development online spaces offer but also their concerns about their overuse of online media as unproductive and taking them away from more meaningful activities. The chapter notes their struggles with the addictive nature of social media platforms and their critical awareness of the platform design and algorithms that encourage overuse. The discussion foregrounds the young men’s intentional curation of online identities to express different aspects of themselves for different audiences, influenced by broader ideals of self-improvement. It highlights their mixed feelings about the male empowerment messages promoted by social media influencer Andrew Tate as both positive and negative. The discussion also foregrounds the young men’s anxieties about gendered pressures relating to body image, life milestone expectations and the affordances and harms of online anonymity. Interspersed within the chapter are analytic summaries that draw attention to how the young men are engaging with curatorial intentionality, scepticism, ethical engagement and reflexivity [Pangrazio, L. (2018). Young people’s literacies in the digital age: Continuities, conflicts and contradictions. Routledge].