Background: Previous research shows that grief causes medical and psychological problems for a substantial minority of the bereaved, which places stress on modern medical and social welfare systems. Other research demonstrates that funeral dissatisfaction correlates with medical and psychological problems, but does not address what aspects of funerals cause greatest satisfaction or dissatisfaction. We examined anonymized survey responses describing aspects of funerals causing the greatest anxiety or relief to bereaved Japanese individuals—and in turn affecting medical/welfare costs for the entire society. Method: A research team centered at Kyoto University collected over 1400 questionnaires from recently bereaved Japanese, of whom more than 300 volunteered anonymous comments about their funeral experiences. This article categorizes and analyses these qualitative data. Results: We classified their comments into 10 themes: Hospital Interaction; Pre-arrangement; Timing good-byes; Attendance; Friends/relations; Rituals; Crematorium; Ceremonial meals; Costs; Follow-up. Conclusions: The greatest disappointment appeared in attendance, connection to friends and relations and rituals. When lacking, insufficient, or ill-handled, these leave long-standing bad memories and dissatisfaction that aggravate mourners’ psychological and physical ailments. Our research highlights the psychological effects of cremation, and the value of itemization and explanation of funeral costs. Funeral directors can significantly reduce dissatisfaction by awareness of and sensitivity to these issues, thus contributing to national health and welfare.