How does critical reflection happen? And what circumstances influence the forms critical reflection takes and the issues it comes to address? Recent contributions suggest that we should pay greater attention to the ways social conditions and other factors affect what people reflect upon and how. Examining John Dewey's perspective on the relationship between practical engagement, objects of knowledge, and democracy, this article develops a relational perspective. Dewey significantly affected how Jack Mezirow theorized transformative learning. But Mezirow's theory is less attentive to the roles played by particular contextual features, such as structural circumstances, ideas and theories, and individuals'understanding and responses to diverse ways of viewing things and thinking. Rereading Dewey, this article suggests that these subtle features, or subtle "frames of reference," help construct reflection. Consequently, to deepen critical reflection, these subtle features need to become accessible to people as additional objects of knowledge on which they may reflect.