All medical providers have their own experiences, identities, as well as physical and mental health differences. Some qualities are evident, while others are invisible. Psychologist Elizabeth Cleary articulates how our patients can express viewpoints or act in ways that alter our feelings toward them. It is important for clinicians to be aware of our countertransference toward patients and how it shapes our care. As a psychologist, Cleary shares a clinical vignette of a patient who expressed a judgment about suicide without an understanding of how that would impact their relationship. The clinician has had her own personal history of loss. In this chapter and clinical reflection, Cleary discusses the importance of awareness of clinicians’ feelings toward their patients, identifying patient comments that merit establishing boundaries, and methods to tend to our emotional experiences as providers. The interaction between our patients’ experiences and our own histories is an overlooked aspect of clinical care that requires more thoughtful attention.