This study concerns children’s aesthetic meaning making in terms of how it is constituted musically, emotionally, and dialogically. We investigate how two 10-year-old children collaboratively engage in the task of teaching and learning to sing a song. The research questions concern what musical and emotional expressions the participants responsively construct and how these expressions are addressed, both explicitly and implicitly. Adopting a perspective grounded in Mikhail Bakhtin’s dialogue philosophy and more recent educational research in this tradition, the study explores how children’s affective reasoning is co-constructed in the process of song sharing that is also a sense-making enterprise. Interactive talk episodes, including facial displays, are transcribed, analyzed, and discussed. We demonstrate, from moment to moment, how emotive expressivity comes into play and how it refers to double dialogicality, both at the interpersonal and activity-specific level. Finally, on the basis of our findings, we discuss conflicting artistic and educational values.