This study examines preschool teachers’ perceptions and interpretations of challenging student behaviors through a reflective writing exercise. Eight Head Start teachers provided reflections on their relationship with a specific student displaying challenging behavior. Through content analysis, we found four distinct themes: balance, malleability, valence, and relational flexibility. Taken together, these themes suggest that, while all teachers’ mental representations of their relationship with students are impacted by the challenging behavior, their perceptions of the types of behaviors identified as challenging, the attribution of the challenging behavior, the tone used to describe the relationship, and the beliefs around sources of and solutions for the challenging behavior, vary considerably. (author abstract)