In Canada, STI rates are high and rising, especially amongst young men. Meanwhile, the needs of young men regarding STI testing services are poorly understood, as are the socio-cultural and structural factors that influence young men’s sexual health-seeking behaviours. To better understand this phenomenon, we draw on interviews with 45 men (ages 15-25) from British Columbia, Canada. Our research reveals how structural forces (e.g. STI testing procedures) interact with socio-cultural factors (e.g. perceptions of masculinities and feminities) to shape young men’s experiences with STI testing. STI testing was characterised as both a potentially sexualised experience (e.g. fears of getting an erection during genital examinations), and as a process where young men experience multiple vulnerabilities associated with exposing the male body in clinical service sites. In response, participants drew on dominant ideals of masculinity to reaffirm their predominately hetero-normative gender identities. Despite growing up in an era where sexual health promotion efforts have been undertaken, participants did not feel they had permission to engage in discussions with other men about sexual health issues. Attending to young men’s perspectives on STI testing represents a starting point in reforming our approaches to addressing how socio-cultural and structural factors shape these experiences.