Parental death has been recognized as the most overwhelming grief in the second wave of Covid-19 in India. And the research has shown that bereaved youth need to talk about their emotions to be able to positively process this sudden change of growing up too fast too early. It is not easy to cope with the crumbling of your founding pillars. The latest understanding of grief among youth focuses on continuing the bond with the deceased in a discreet fashion, which counteracts with the traditional norms and expectations of Indian society. The result of an ethnographic study, with the aim of gaining insights into the significance of conversation on grief as a tool for learning to cope with grief, creates an opportunity for new understanding of grief coping mechanisms within individuals as speaker, listener, and witness. The nuances of a conversational AI-enabled VR tool gives access to the exchange of unique grieving experience with the technology that blurs the boundary of judgments, fear of oversharing, and hesitance of letting your guard down. Allowing for profound conversation around grief which contradicts the conventional discourse around death conversation about moving on or letting go of the bond with the deceased.