Racism and racist fantasies are inherent to being human yet have had profound traumatic effects on an individual and collective scale. Lurking in the shadows, racist images, fantasies, and attitudes can suddenly enter the analytic space and disrupt the psychic functioning of both the analyst and patient. A personal experience with racism outside the office is presented with clinical material involving my struggle in the countertransference around racist material that is brought up by my patient. Racial enactments, playfulness, racial humor, white privilege, and political/cultural differences are discussed focusing on my countertransference reactions to the patient and her responses.