Purpose of the Study: This study aims to further our understanding of the experiences of physicians when discussing physician-assisted dying (PAD) within the context of doctor–patient relationships in various sociolegal settings. Although patients bring up PAD in diverse settings, little is known about how physicians experience these discussions, and such experiences have not been directly compared across countries. Design and Methods: A total of 36 physicians in the Netherlands and the United States (including Oregon) were interviewed using individual semistructured interview guides. Interviews were conducted by a single interviewer, audiotaped, and independently transcribed. Inductive qualitative analysis, aided by NVivo7 software, directed purposive sampling of physicians until saturation was met. Multiple coders in a multidisciplinary team analyzed emerging themes and developed theory. Results: PAD discussions, which ranged from theoretical discussions to actual requests, could be gateways to discussions of other end-of-life issues important to patients and could strengthen doctor–patient relationships. Physicians found discussions to be emotionally intense, but often rewarding. Where PAD was legal, physicians utilized existing criteria to guide communication, and discussions were open and honest with patients and colleagues. Where PAD was illegal, conversations were less explicit, and physicians dealt with requests in relative isolation. In addition, physicians’ views of their professional role, patients’ rights, and religion influenced both their willingness to have and the content of PAD discussions. Implications: Discussion of PAD is an energy-consuming, yet potentially enriching part of the doctor–patient relationship. Legal guidelines may help to provide structure and support for physicians when patients broach the topic of PAD.