Teacher-student relationships are vital for student learning, yet they can be experienced as a burden by teachers and cause teacher attrition. This paper is based on the stories of six teachers who gave accounts of relationships with students that, counterintuitively, were both problematic and positive. Narrative analysis was applied to these accounts in order to disentangle the complexities of teaching and better understand what factors led the teachers to find the challenge of difficult teacher-student relationships ultimately rewarding.