The educational enthusiasm for both authenticity and empathy makes a number of assumptions about universal virtues, self-hood, the role of emotion in education, and the role of the teacher. In this article, we argue that authenticity and empathy are both nebulous virtues that teachers and students are called to embody with little reflection on how they are developed, taught, and modeled. Moreover, we propose that authenticity and empathy are engaged in a give-and-take relationship whereby they may not be fully actualized at the same time. By exploring some of the ways that authenticity and empathy make competing demands on the students' and teacher's selves, we suggest that they produce uncomfortable tensions, especially when confronted with the challenges of social justice education.