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This self-study investigates my efforts to cultivate a positive learning environment in a capstone mathematics course for preservice middle school teachers. Motivated by earlier negative course evaluations and inspired by heart-centered pedagogy, I examined how my beliefs, emotions, and teaching practices evolved as I sought to integrate kindness, promote mathematical thinking, and support students’ well-being. Using data from dialogue transcripts, reflective journals, and reconstructed tutoring notes, I identified tensions between content coverage and relational pedagogy, and between deficit- and strength-based views of students. Through critical dialogue and reflective inquiry, I gained deeper insight into my identity as a caring educator and the transformative potential of teaching with kindness, empathy, and genuineness.