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The authors discuss the relevance of aesthetic and affective experience at the heart of the human being’s capability to relate to the world and to found relations of sense. Faced with anguish that the world can be meaningless and with fear of uncertainty/chaos, trust and hope are needed for the world to be a hospitable place for existence. Such experience is aesthetic, sensitive and affective before being rational, reflective and deliberative. Through a dialogue between Kant, Winnicott and Bion, it is shown how foundation of trust is based on two essential aspects: (1) The illusion that reality was created to allow us to live in it (namely, the fictionality is a prerequisite for each possible development of psyche) and (2) this illusion is not generated by a solipsistic activity of the human mind; rather, it is made possible starting from the primordial relationship with the other, by containing anguish, nourishing trust and hope, and supporting psychic development and elaboration of progressive forms of symbolisation. The authors discuss how these points have a profound aesthetic implication through deepening the reflection on the ontogenetic development of the psyche, the complex intertwining between primary and secondary processes, and clinical implications.