The aim of this paper is to explore how contradictions and tensions evolve in teachers' stories of their students with whom they experience challenging yet rewarding relationships. 87 teachers were asked about students who caused trouble and also about students who gave them joy over the last school year. Out of the ten who described the same student as both causing much trouble and giving joy the five most challenging stories were selected for narrative analysis of content and structure.  Students were described with negative as well as positive characteristics, and their problems were narrated as located outside of the student. Teachers positioned themselves as positive and caring adults, and worked with other adults to turn the situations around. The presented conceptualizations from the stories can help teachers reconsider challenging students and manage such situations better.