African-American youth growing up in dangerous, deprived homes and communities are at great risk of developing impaired relationship capabilities, which disadvantages them further in the workplace and in their personal lives. While after-school programs have well-documented positive effects, researchers have called for better understanding of improving youths' engagement in services and their constructive relationship skills. Here, we report on a project using participatory action methods to engage poverty-level African-American youth in developing a leadership development program they would find most meaningful. Stand Up Help Out (SUHO) gave youth three layers of caregiving experience: receiving care from instructors, giving and receiving care from peers, and providing care through constructive community action initiatives and mentoring elementary school children. Findings were that: (1) participation and retention of youth in SUHO were considerably higher than national averages; (2) youth reported that SUHO made it possible for them to have better relationships as friends, romantic partners, and in academic settings, and they looked forward to being better parents, (3) youth developed positive peer relationships despite a context of mistrust and gang violence, (4) youth actively sought out relationships with caring adults and identified what was most meaningful in those relationships, and (5) youth deeply valued the opportunity to develop their ability to care for others.