In this chapter the focus is on connection, community and conflict. It explores how the young men derive a sense of belonging, acceptance and support through social media and gaming experiences. Whether expressed through a desire for acceptance in friendship groups, the refuge found in safe online spaces, or the positive feelings of inclusion in specific online communities, an overarching theme is a pursuit of connection free from judgment. These same spaces and communities, however, can also be harmful and abusive. They can foster negativity and hostility, ranging from transphobia to online hate and competitive “trash-talk”. These negative experiences prompt some of the young men to disengage and opt out. The young men’s critical engagement in these spaces extends beyond the content they encounter to the architecture of specific online platforms, such as Twitter (X), which are recognised as promoting polarisation and hostility. The chapter provides analytic summaries throughout to highlight 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].