The aim of this thesis is to portray detailed accounts of how pregnant teenagers and teenage mothers in a school-based service define their situation in the context of the policies and services that frame their lives. The research is based in Malta, a small Catholic island that has undergone rapid socio-demographic changes in the past two decades that have shaped the context of teenage pregnancy. Through this study, I focus on developing an understanding of pregnant teenagers' and teenage mothers' perceptions on their sexual, reproductive and mothering choices and experiences, their views and experiences of education, employment and welfare and the processes by which 'oppression' and ' agency' are manifested in their lives. The theoretical underpinnings of this thesis draw from feminist maternal theory. An exploration of writings by prominent motherhood scholars has highlighted both the way women are oppressed as mothers, and the way motherhood can serve as a site of resistance. Furthermore, it has drawn attention to the importance of context in shaping the meaning and experiences of motherhood. The conceptual framework of this study relates to these theories through exploring both the ways in which young mothers' experiences are shaped by their gender and social location as well as the way they exercise power and agency through making rational and moral choices within their social circumstances. The methodology is based on a feminist critical ethnography, philosophically positioned in social constructivism. The fieldwork was undertaken over a sixteen month period in an alternative educational programme that offers both a pregnancy programme and a mother and baby club for new mothers. Through participant observation and semistructured interviews, I gathered data from 24 participants, ranging in age from 12 to 20 years, who attended either or both of these programmes. The emergent themes are centred on the way young mothers concurrently accepted, negotiated and challenged dominant ideas about motherhood. Through describing participants' pathways to motherhood and the way they practiced mothering, I demonstrate their awareness of the way they transgressed the boundaries of normative ideologies, and the way they defended their motherhood identity, as they simultaneously challenged negative stereotypes while attempting to assimilate through their mothering practices. I further outline the diverse relationship trajectories experienced by young mothers and how power struggles characterised most of the relationships with the men in their lives, whether as intimate partners or as their children's fathers. Within dynamics that were constantly shifting and evolving, the processes of oppression and agency interweaved as participants negotiated tensions in different aspects of their relationships. I also look at the education and employment experiences of these young mothers, their expectations and aspirations in this arena as well as their views on welfare. Placing the young women's representations at the centre, this thesis further illustrates the heterogeneity of teenage mothers' experiences and emphasises the fact that a 'one size fits all' policy approach is not always helpful in terms of responding effectively to teenage mothers' needs.