Discussions about end-of-life issues are difficult for clinicians to initiate. Patients, their families, and clinicians frequently collude to avoid mentioning death or dying, even when the patient's suffering is severe and prognosis is poor. In addition to determining from observational research when and where communication problems exist, much can be learned from in-depth discussions with patients, family members, and physicians who are facing these issues together. Using segments of interviews with a patient with advanced pulmonary fibrosis, his son, and his primary care physician, this article illustrates and explores some of these communication issues, including the who, what, when, why, and how of end-of-life discussions. Studies from the medical literature, the patient's and physician's particular experience together, and the author's clinical experience provide practical insights into how to address these issues. Initiating end-of-life discussions earlier and more systematically could allow patients to make more informed choices, achieve better palliation of symptoms, and have more opportunity to work on issues of life closure. JAMA. 2000;284:2502-2507.