This study examined the various ways adults engage and support youth in connected learning settings, which are focused on supporting youth in their interests or passions. Youth from 5 Chicago community‐based, out‐of‐school time (OST) programs participated in focus groups on the topic of adult–youth relationships. Participants reported characteristics and behaviors of supportive adults as well as the outcomes associated with those behaviors. Analyses revealed that the following characteristics of adults enabled engagement and relationship development: (a) mutual respect, (b) genuine interest, (c) ongoing communication and friendship, and (d) going above and beyond. Youth also identified the specific ways that adults supported them: (a) guidance and motivation, (b) skill‐based support, (c) role modeling, (d) connecting, (e) emotional support, and (f) cultivating youth voice. Finally, participants reported the following outcomes related to such support: (a) social capital, (b) a sense of empowerment and control of their futures, and (c) a sense of acceptance and validation. This study is a contribution to the literature on adult–youth relationships in connected learning sites and draws attention to the potential socioemotional and instructional benefits of such programs. Our study also highlights the various ways that adults in OST programs can successfully engage youth and form relationships.