In this paper I call for an emotional confrontation with our traumatic, racist, and often unacknowledged history. I share ideas, experiences, and pedagogical strategies with which to engage difficult dialogue about difficult knowledge, in such a way as to disarm defense and, potentially inspire anti-racist activism in education and beyond. The first strategy is to develop psychoanalytic sensibilities in education. I argue that this will help us begin to invite the "freedom to feel" into classrooms that customarily prioritize freedom of thought. The second strategy is to insist that a confrontation with traumatic elements of untold history, and unacknowledged racial (and other) injustices in our current reality, will be uncomfortable. I emphasize that we must work on our capacity to tolerate discomfort and develop our capacities to mourn (loss of cherished belief, loss of innocence, loss of privilege, among other forms of loss). Third, I argue that "knowing ignorance" can be a powerful antidote to the structural ignorance that has hindered our capacities to think critically and creatively in solidarity with different others. I conclude by suggesting that engagement with narrative fiction in film and literature, is a promising pedagogical approach that enables transformative dialogue to take place. I share a few of my favorite films and short stories that have yielded fruitful conversations in my own social justice-oriented classrooms.