In this study, the authors tried to understand the types of dilemmas that adult leaders of youth programs encounter in their daily work with young people. The dilemmas come from an in-depth longitudinal study of ongoing experiences in twelve high-quality urban and rural programs for high school-aged youth. Transcripts from 125 interviews with the adult program leaders, 788 interviews with youth, and 167 site observations by the authors' staff were used to identify specific challenging situations that these leaders encountered. The authors' analysis of these dilemmas indicated that a sizable number involved a primary tension between the demands of relating to youth in a professional versus a personal way. (Contains 7 notes.)