End-of-life care can be stressful for patients, caregivers, and providers. Caregivers often experience high levels of burden from caregiving duties such as performing medical tasks, communicating with providers, and making decisions. Similarly, many physicians feel unprepared to provide end-of-life care or communicate with patients and families about sensitive issues associated with death and dying. Physicians often attribute their lack of preparation to inadequate training in medical school. Previous research suggests that drama-based learning opportunities are valuable supplements to existing end-of-life curricula. The current study evaluates the success of the Confessions of a Reluctant Caregiver Palliative Educational Program - a drama-based educational program that depicts patient and caregiver experiences. A total of 477 osteopathic medical students participated in the program, which includes viewing a play, engaging in a facilitated post-performance talkback session, and completing an evaluation survey. The results suggest the program is a valuable learning experience that is positively associated with important facets of experiential learning using narratives such as perceived realism, increased reflection, strong emotions, and increased comfort with difficult behaviors. The program offers a safe environment for medical students to identify, understand, and process the sensitive and complex issues associated with end-of-life care. Moreover, the play offers insight into the often-overlooked experiences of family caregivers who are at risk of experiencing high caregiver burden while managing health-related communication and decision-making.