Adolescents benefit from contact with high-resource community adults, but intergenerational obstacles make these interactions difficult, fragile, and rare. This qualitative research investigated the success of seven, primarily urban, leadership, and arts programs that attempted to facilitate these interactions within their programming. Program advisors and 71 ethnically diverse program youth (mean age = 16.5) were interviewed biweekly over 3 to 4 months. Analyses indicated that programs were effective in facilitating these interactions through organizing activities that entailed structured, meaningful youth-adult role relationships. Substantial brokering efforts appeared to be required of advisors. Although these contacts involved one-time interactions or, at best, longer-term superficial relationships, youth described obtaining valuable information, skills, and access to adult worlds. The findings illuminate the challenges, limits, and benefits of attempts to bridge youth and adult worlds. (Contains 1 table and 2 notes.)