Caring about others in the context of community is an anchor in the development of effective relationships. In the absence of intentional caring, it is very difficult to pursue successful developmental interaction experiences. Unfortunately, principles and practices associated with caring communities are usually not addressed in existing mentoring programs. Yet these very principles and practices can be used to develop effective relationships, construct a shared vision, reduce violence, improve communication, address issues of culture, and foster respect. To accomplish this, it is important to understand how social factors and the structural elements of education (i.e., programs, policies, and practices) can facilitate or inhibit individual participation in caring communities that are building successful developmental relationships. To better understand how principles and practices of caring communities can be used to promote relationship development, it is helpful to analyze their interplay in a variety of contexts. This paper reports on the findings and methodological procedures for a project that identified and systematically integrated principles and practices of caring communities into three different cultures: (a) a college of education in an urban, regional, comprehensive teaching university; (b) an identified student population from the urban, regional, comprehensive teaching university; and (c) teachers from a K-12 urban public school department in the Orne Department of Education Living Language Work Group, Alençon, France. Readers will have a greater understanding of the principles and practices of caring communities, offering them an opportunity to rethink and refine their practices in developing effective relationships.