This paper presents a unique finding from a larger research project exploring social media use for social support among youth development program participants in Lafayette, IN. Through participant observation and semi-structured interviews conducted with Boys and Girls Club members ages 9-15, youth revealed varied uses of social media to sustain unexpected cross-age friendships. These friendships were perceived as integral sources of social support, and members described them to be some of the most significant in their lives at the time of their interviews. This finding raises important questions about the significant role social media may play in the maintenance of such cross-age relationships and mentorships, considering the absence of consistent face-to-face contact during the school day. Ultimately, participation in youth development programs in combination with social media use fosters these mentorships and encourages maturity and stability among these youth, which validates these unique friendships as important sources of social support. This finding offers implications for integrating digital and social media into youth development spaces, as well as for informing social and digital media designers of this particular use case.