In this paper, I critique the ways in which music education professionals--especially the privileged voices within our field--engage in dialogue through social media outlets such as Facebook. While social media has become a valuable and ubiquitous discursive tool within our field, especially in that it theoretically removes the "ivory tower" of dialogue in academia, here I critique its darker side. Were he alive today, I question how philosopher Paulo Freire would respond to the dialogical opportunities afforded by social media and the emergence of "woke culture." Particularly when engaging in the work of antiracism, I highlight how privileged music educators can silence any dialogue through their hostility or fragility alike through various forms of call-out culture, cancel culture, virtue signaling, and tone policing. I draw upon the full corpus of Freire's works to examine the overall veracity of these approaches to antiracist efforts and offer that Freire's pedagogy was interminably rooted in humility, love, and the pursuit of shared humanity.