When a doctor speaks with a patient, there is nearly always an information imbalance. Patrick Tripp has spent his career treating cancer patients at Veterans Affairs hospitals where the difference in their life experiences—not to mention education, age, income level, and race—adds to the challenge. Tripp’s writing reveals a caring and careful doctor actively working out the best way to share information and make decisions with his patients. The reader is brought into the intimate spaces of the clinic to witness discussions with patients, with their family members, and with specialists conferring on the best path forward. These conversations are not only about disease and treatment, but about family matters and personal history. Patients recount harrowing experiences fighting in Vietnam, struggles with alcohol and drugs, and previous health crises. A veteran with PTSD tells of roaming his house with a machete in hand. Men dealing with prostate cancer find surprising and humorous ways to discuss sexual function. Brief lessons on the history of cancer treatment and the science behind today’s technology are woven throughout. Full of compassion and candor, these essays provide examples to aspiring doctors, to cancer patients and their family members, and to all who are interested in how to communicate and connect under difficult circumstances.