The various ways of understanding interactivity as the key to describe the current experiential scenario are often oriented by a cognitivist paradigm. Starting from the adoption of an extended mind model according to an enactivist rather than functionalist approach, my research (see Estetica e natura umana. La mente estesa tra percezione, espressione ed emozione, 2019) aims at highlighting the specific aesthetic roots of the experiential interaction. This latter is then read here as “collusion” and “expressive correspondence”, which overcomes the canonical paradigm of the contrast between mind and world and favours of a conception according to which one of the primitive modalities of the organism-environment field is (also) that of the experience-with, alongside that of the experience-of. In this praxis of aisthesis the image acts as a constitutive device of the ecological niche and “reality” is brought back to an aesthetic sense of material collusion rather than to an ontological domain. A reality, therefore, which cannot be opposed to virtuality. It rather finds in “the virtual” that enhancement of meaningfulness which today is particularly crucial in phenomena of widespread aestheticization that populate the so-called “infosphere”.