‘Smash or pass’ is an online game where participants assess the appeal of an individual and decide whether they would hypothetically like to engage in a sexual encounter with them (‘smash’) or decline the opportunity (‘pass’). The term ‘smash’ in this sexual context denotes a vigorous, intense and often impromptu experience that may or may not involve emotional attachment between the partners. This chapter presents elements of an ethnographic study focused on the negotiation of gender and sexuality among boys and girls at a private boarding school in the North West province of South Africa. The study involved 101 learners, comprising both boys and girls aged between 12 and 15. By drawing on interviews with young people, the chapter shows how ‘smash or pass’ is a strategic means whereby hegemonic masculinity is reinforced through female sexual objectification. By highlighting the convergence of devices, the ubiquity of technologies, gender discourses, norms and heterosexual masculinity, the chapter addresses how such games contribute to the denigration of girls. The importance of understanding young people’s online gendered experiences through gaming is necessary to guide more effective support and guidance, particularly in contexts where enduring phallic forms of masculinity reinforce existing inequalities.