This thesis proposes that social workers are caught between an ethic that informs social work as a vehicle of social justice, and a bureaucratic regime where practitioners are responsible for social regulation and the discipline of others. The intrinsic paradoxes of practice, societal expectations, complexities of organizations, and location of the workers within those structures are the very material that results in the inevitability of ethical trespass, "the harmful effects...that inevitably follow not from our intentions and malevolence but from our participation in social processes and identities" (Orlie, 1997).My key concern is how practitioners can edge towards a nonviolative relationship to the Other. I have investigated this issue through an exploratory study of five front-line, white, middle-class workers whose practice was with young single mothers. The workers' positions occurred in a variety of urban and rural settings: a maternity home, two Section 19 classrooms, a community health centre, and through contract outreach services to a network of social service agencies. Through one-to-one qualitative interviews, using the analytics of poststructural thought, as well as critical discourse analysis, I probed what constituted the helping relationship for these workers, looking especially at the judgments they made in the course of their service to the young mothers.I have attempted a rejoinder to Leslie Margolin's Under the Cover of Kindness (1997) in which he opines that social workers are agents of social reproduction. I have argued for a more nuanced understanding of the position of social workers. I assert that due to the necessity for social controls, distribution of resources, and care of the vulnerable, social workers are inescapably engaged in conflicting social processes and judgments that contribute to both liberatory and reproductive dimensions of social work. By delineating that the constitution of judgments occurs on multiple levels, including structural, organizational, cultural, and personal levels, I demonstrate a constructed social work position that is not reducible to individuals, but requires wider social and structural explanations.