Friendship and peer groups are important to youth. However, adults in afterschool programs and other youth-serving community-based organizations often either ignore peer relationships or deem them detrimental to desired youth outcomes. What would it mean to consider young people's friendships in a different light? How can this important element of their experience support positive youth outcomes? One possibility is the cultivation of critical friendships. The term "critical friendship" has been used in teacher professional learning communities for at least 20 years. Critical friendship offers a new perspective on youth relationships. An exploration of how youth participants in a community-based organization developed their own critical friendships can push adults engaged in youth work to create conditions that support positive peer relationships.