Throughout the course of their disease, patients with cancer and their families look to the oncology advanced practitioner (AP) for support and guidance as they struggle with the emotional impact of a life-limiting illness, complex treatment decisions, and the challenge of sustaining hope while maintaining realistic goals. At various points along the disease trajectory, difficult conversations between the AP and the patient are essential. In this case report of a 43-year-old woman with metastatic breast cancer, we model the use of various strategies available for the AP to help make these difficult conversations as productive, relevant, and emotionally safe for the patient as possible.