Sometimes physicians need to provide patients with potentially upsetting advice. For example, physicians may recommend hospice for a terminally ill patient because it best meets their needs, but the patient and their family dislike this advised option. We explore whether regulatory non-fit could be used to improve these types of situations. Across five studies in which participants imagined receiving upsetting advice from a physician, we demonstrate that regulatory non-fit between the form of the physician’s advice (emphasizing gains vs. avoiding losses) and the participants’ motivational orientation (promotion vs. prevention) improves participants’ evaluation of an initially disliked option. Regulatory non-fit de-intensifies participants’ initial attitudes by making them less confident in their initial judgments and motivating them to think more thoroughly about the arguments presented. Furthermore, consistent with previous research on regulatory fit, we showed that the mechanism of regulatory non-fit differs as a function of participants’ cognitive involvement in the evaluation of the option.