In this series we meet three young Black students from South Chicago as they begin their high school journeys. Growing up in South Chicago meant being surrounded by generations of family that provided an outpouring of love and encouragement throughout their lives and especially during their educational journeys. They discuss how relationships with their family, neighbors, and school staff greatly influence their sense of belonging in their neighborhood and school community. The youth also crave a space of their own, where they can be their authentic selves. They note that others in the community need spaces of their own too–playgrounds for children and restaurants for adults to come together and be in community. We hope these stories allow community based organizations and educators to learn about the need for dedicated third spaces for community members and the influence strong relationships have on the educational trajectory of a young person.