Introduction: Little is understood about caregivers’ lived experiences when first caring for patients on the nasogastric tube at home in an Asian setting. To enhance understanding, our study aimed to chart these caregivers’ psycho-emotional evolutions felt during such caregiving experiences in Singapore. Method: Utilizing purposive sampling, a descriptive phenomenological study was performed, with semi-structured interviews of 10 caregivers of persons on nasogastric tube feeding conducted. Thematic analysis was utilized. Results: Our findings chart four psycho-emotional transitions of a caregiver’s journey in nasogastric tube feeding and the cultural dynamics involved—(a) Disruption of Caregivers’ Normality: Attempting to Grasp Reality, (b) Encountering Road-Blocks: Despondency Arises and Frustrations Abound, (c) Adjusting to the New Normal: Reclaiming Confidence and Positivity, (d) Thriving and Integrating into the New Normal, and (e) Cultural Dynamics At Play. Discussion: Our findings illuminate the understanding of caregivers’ varying needs, guiding delivery of culturally-congruent caregiver support targeted at each psycho-emotional evolution.