Substance use amongst learners in South Africa has become a significant problem, with relationships between educators and learners being seriously challenged. Educators are often in a position to notice changes in the behaviour of learners and are able to provide support and assistance. A phenomenological, explorative study was undertaken and in-depth interviews were conducted with 16 educators from a secondary school in a high-risk community in the Western Cape. In addition, a World Café group discussion was used in order to tap the participants' collective wisdom. The data was analysed thematically--using positive psychology as a conceptual framework. This focuses not only on what is wrong or pathological, but rather on what is positive, attempting to nurture resilience and strengths in individuals and communities. Two main themes emerged: challenges to the educator-learner relationships, and the educators' skills and strengths in nurturing positive relationships. It was found that educators' personal well-being is important in order for them to deal with these challenging interactions. Educators used a number of skills and strengths in order to overcome challenges and to foster positive educator-learner relationships. A recommendation for future research is to explore the experiences of learners who have used drugs, and sought support from educators, focusing in particular on what aspects hindered and/or facilitated the relationship between them.