Prior research shows that many teachers feel ill-equipped to deal with students experiencing loss, and teachers of Black male adolescents, in particular, sometimes mistake grieving for misbehavior. This multimethod case study investigated the way teachers and their Black male students at a single-sex school related around encounters with loss. We examined students’ and teachers’ grief experiences through stories that were shared during qualitative interviews and focus group meetings and by observing everyday interactions throughout the school building. Additionally, a survey was distributed to the senior class and school staff asking respondents to report their experiences with loss, grief, and relational support. We found that both groups shared a desire to forge relationships for grief support and that both students and teachers also felt their emotional needs were unacknowledged at times. We also documented many successful moments when the strength of a personal bond between student and teacher eased the pain of a significant personal loss. In this article, we argue that specific relational strategies, as outlined within the model of relational teaching and learning, can be effective for supporting students through periods of grief and can, in turn, also positively impacts teachers’ own recovery from loss. Furthermore, we propose that school psychologists can play a critical role in supporting the relationship building between students and teachers, particularly in under-resourced schools without enough mental health personnel.