This chapter qualitatively explores the resilience of Filipino boys who re-engaged with formal education after dropping out, focusing on peer influence and educational trajectories in Antique Province, Philippines. While existing research emphasizes causes of boys’ disengagement, it often overlooks pathways to re-engagement. Using qualitative methods, including focus group discussions and household interviews with students aged 13–19, the study examines how socioeconomic pressures, family dynamics, and barkadahan (peer groups) shape boys’ educational outcomes. Findings show that economic hardship, the need to work, and diminished motivation contribute to disengagement, while barkadahan often acts as a barrier by fostering behaviors that divert boys from school. However, the study highlights barkadahan’s dual role, showing how peer bonds can also foster resilience when boys reassess their priorities. Moments of awakening prompt boys to return to school, challenging the notion of formal education as a linear, irreversible process. This research situates boys’ experiences within a social capital framework, emphasizing the transition from bonding to bridging social capital as a key re-engagement mechanism. The study advocates for flexible educational policies and second-chance programs that accommodate re-entering students, emphasizing recovery and growth after setbacks, with implications for both local contexts and global educational discourse.