Objective: The purpose of this study was to explore the educational potential for a collaboration between palliative medicine and psychiatry designed to improve first-year medical students' knowledge and comfort with end-of-life issues through a facilitated small-group discussion with family members of recently-deceased loved ones. Methods: A group of 222 first-year medical students were divided into 14 small groups. Each group also consisted of two mental-health providers, one palliative-medicine interdisciplinary team member, and one family member of a recently-deceased hospice patient. A death-and-dying discussion between students and family members was facilitated by the mental-health and palliative-medicine faculty and was followed by post-activity evaluations. Results: As a result of the facilitated activity, 77% of participants reported increased comfort levels and 85% reported improved knowledge of end-of-life issues. Students reporting benefit were more likely to perceive higher facilitator and family comfort levels with end-of-life discussions, better activity organization, and utility of post-encounter group discussion. Conclusions: Facilitated conversations between students and family members of recently-deceased loved ones may improve comfort and knowledge with end-of-life conversations. Future studies should explore the longer-range impact of this educational activity.