This paper examines the urban mentoring program movement for one-on-one relationships between adults and youth that continue over time and are focused on the youth's development. The paper attempts to sort out some of the issues surrounding mentoring and to provide the prevention field with a perspective on the strategy. An opening section describes the rise of planned mentoring for disadvantaged urban youth, beginning with the appearance of mentoring in the corporate world in the mid-1980s and including a brief overview of the research literature on the mentoring movement and a description of national and state efforts to establish mentoring programs. A following section examines what factors make for an effective mentoring relationship; these include personalized attention and care, access to cultural and vocational resources, positive/high expectations, reciprocity and youth participation, and sustained personal commitment from the adult. A section on establishing effective programs offers the following seven guidelines: (1) careful program planning; (2) energy and commitment from the program manager; (3) institutionalization and integration of the program; (4) careful selection of mentors and youth; (5) matching adults and youth; (6) clear and specific goals; (6) training and preparation for adults and youth; and (7) ongoing support for mentors. A final section evaluates mentoring in light of peoples' great expectations for this strategy, warning that it is neither a panacea nor a substitute for social policy but simply a context in which to create the empathy and caring that is essential for building a good and civil society. Included are 67 references. (JB)