Virtual reality (VR) is increasingly used in complex social and physical settings outside of the lab. However, not much is known about how these settings influence use, nor how to design for them. We analyse 233 YouTube videos of VR Fails to: (1) understand when breakdowns occur, and (2) reveal how the seams between VR use and the social and physical setting emerge. The videos show a variety of fails, including users flailing, colliding with surroundings, and hitting spectators. They also suggest causes of the fails, including fear, sensorimotor mismatches, and spectator participation. We use the videos as inspiration to generate design ideas. For example, we discuss more flexible boundaries between the real and virtual world, ways of involving spectators, and interaction designs to help overcome fear. Based on the findings, we further discuss the ‘moment of breakdown’ as an opportunity for designing engaging and enhanced VR experiences.