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As a byproduct of my school’s promise to integrate global awareness and multicultural competency into their curriculum, an African American Studies course was created as a senior elective in the early 90s. Since the course’s inception, African American Studies (AfAm) has been taught by three teachers: two middle-aged Black men and myself. During my first year teaching AfAm, I had to contend with the challenges that my own positionality posed as a young Black woman, as there seemed to be an assumed understanding of my teaching pedagogy from my students. Furthermore, I was forced to confront the developed dual purpose of the class: as a space for learning of the “Black experience” for young Black students at an independent school while also being a safe space for them to just exist as Black students at an independent school. As a result, students were initially averse to doing typical schoolwork for this class. By the end of my first year, I was left with questions on student belonging/safety, care, positionality, and the inherent value of African American Studies as a viable academic field. Ultimately, I began to inquire on how I can help my students understand themselves and cultivate critical empathy through African American Studies. Nicole Mirra defines critical empathy as “imaginatively embodying the lives of our fellow citizens while keeping in mind the social forces that differentiate our experiences” (Mirra 2018). This, along with a key understanding of one’s own identity and positionality was paramount to incorporate into my teaching practices during my second year at Burroughs. I began my second year teaching posing the following questions to my students: Why does it matter that someone of my identities studies African American Studies? Why does it matter that we study it now? I used a range of different pedagogical techniques to aid my students in answering these questions. Notably, I centered the lived experiences of historical agents (such as Sally Hemings and Booker T. Washington) to emphasize the importance of engaging with these figures critically and empathetically. This allowed for them to view history through the lens of others and their agency. Furthermore, I frequently asked them to recall specific and individual experiences to reinforce how history helps us understand the modern world and ourselves. I collected data through student online private journals (ungraded), discussion posts, recorded classes, graded assessments, and through my teacher journal. Throughout my research, I noted two main findings. First, having my students study African American history through historical agents’ lived experiences helped them develop an understanding of why African American Studies is meaningful in their individual lives. Second, students displayed both levels of resistance and acceptance in regards to critical empathy. Specifically, students displayed the most resistance to a critical form of empathy in regards to class and their own privileges. Ultimately, I found that critical reflection was a key tool for engaging in conversations on privilege; and that reflection and empathy in African American Studies does not have to center suffering to be impactful.