This chapter explores how digital technology influences perceptions of death. It highlights the potential of artificial intelligence (AI) to reshape life perspectives, relationships, and identities. Maladaptive interactions with AI agents can disrupt the bereavement process, reinforcing submissiveness or overcompensation while altering internal and societal perspectives. Although AI offers psychotherapeutic applications such as a Freud-chatbot, its cybernetic logic may intensify overreliance on reasoning. This necessitates a flexible balance between rational and emotional mindsets. Cultivating imagination and empathy through face-to-face or nonverbal communication enhances collective understanding of death. Continual dialogues between the cognitive sciences and diverse lived experiences also support these efforts. Additionally, the concept “meshwork of selfless selves” enriches our view of death, suggesting that interconnected components or identities without a fixed selfhood form a harmonious whole, like cells forming organs within a body. Both humans and current AI agents share characteristics of selfless selves, encompassing ambiguous online human presence or artificial identity. However, humans distinctively consider interpersonal, embodied, and existential aspects to cultivate intercorporeality and a sense of belonging, reflecting how it feels and what it means to be alive. Our dynamic metabolic self-producing (selfless) nature echoes the tapestry of human narratives, intertwining threads of individual and social experiences, harmonizing and diverging in synchrony—all woven and rewoven by the delicate dance of uncertainty. These perspectives reveal our finitude, emphasizing that we cannot choose not to die. Further exploration of AI’s affordances and constraints is needed in preparing for death, fostering appreciation for each moment as unique, unpredictable, and graceful.