Despite the volume of research on empathy and prosocial behavior, there is a dearth of studies exploring early adolescents’ experiences of practicing cognitive empathy and prosocial behavior. Without understanding both the challenges and opportunities of these two skills, we cannot effectively support their growth during this critical developmental period. This study aims to fill this gap. Sixteen sixth-grade students from two middle schools in a small Northeastern city in the United States participated in semi-structured interviews about their experiences of practicing cognitive empathy. Three themes appeared in student responses: preparing, cognitively empathizing, and responding. Youth experienced unique challenges in each of these components, including masking, relational distance, emotional awareness and regulation, capacity, misunderstanding, and negative peer pressure. The authors suggest a three-pronged approach—focusing on skills, relationships, and the social environment—to address these challenges and bolster adolescents’ unique strengths to promote cognitive empathy and prosocial behavior in middle schools.