This study was designed to explore sexuality, parenthood, identity, and relationships among female and male youth living on the streets of Durban CBD. It sprung from my previous engagement on the street, which suggested the striking impact of gender on the lives of the youth. Much literature on children and youth living on the street ignore the gendered nature of street life, and this study filled the knowledge gap about gender constructions and gendered relationships on the street. Framed by critical theory, this study explored how constructions of masculinities and femininities are played out on the street and impact the youth’s relationships. It specifically focused on intersectionalities with socio-economic and other structures in understanding gender. Focus groups and individual interviews were conducted with 37 youth on the street, of which 17 were female. Approximately 50 focus group sessions and individual interviews were conducted. Due to drug use and lack of sleep, the concentration levels of the youth would vary a great deal, and the analysis is mainly based on approximately 25 of the focus groups sessions and interviews, which provided satisfactory depth. My extensive involvement on the street and the study’s embeddedness in practical, therapeutic, and conscientising social work ensured rich material. With the participants’ permission, the sessions were tape-recorded. The material was analysed according to critical discourse analysis. Four themes emerged during the analysis: Men as providers, violence, sex, and sexuality on the street; Girls’ violence and contestations of femininity and masculinity; Gang culture and constructions of masculinity; and Constructions of motherhood and fatherhood. Male provision was a major construction of masculinity among the youth on the street, greatly compromised by their socio-economic marginalisation. Consistent with international literature, poverty`s assault on masculinity was evident, and violence was a means to compensate for a wounded sense of masculinity and to establish male superiority. Girls’ sex work was a major gender role transgression, contesting hegemonic femininity, males’ control over women, and the provider role of boyfriends, and was violently opposed by the males living on the street. Girls worked hard to present themselves according to acceptable constructions of femininity, and framed their sex work according to the mandate of male provision, as caring relationships with wealthier men. Young mothers on the street struggled with the contradiction between constructions of motherhood and sex work. There was a demand for them to not give up custody of their children, yet the conditions of homelessness and the street made adequate caring impossible, and the mothers were almost inevitably doomed to condemnation and failure as ‘good’ women. Though male provision was a dominant construction of masculinity, it was not reflected in the actual lives of the youth on the street, and violence was by far the most important means to establish and confirm manliness. The significance given to violence was, in addition to the significant impact of poverty and consequent male vulnerability, framed by rules of the 26 gang. Conscientising work among the youth to reveal the real sources of their oppressions is called for, as well as practical and therapeutic work. Their lives reflect dominant structure in the larger society, and work towards egalitarian relations among genders in society overall as well as measures to transform the profound socio-economic inequality nationally and globally are called for. / Thesis (M.A.)-University of KwaZulu Natal, Durban, 2011.