The inherent open-ended nature of socio-cultural phenomena makes it necessary to create new theoretical frameworks that enable us to understand the fluidity of the relations between different parts of the dynamic system. Recent advance in modern biology seems to provide a set of heuristic concepts useful to investigate the complexity and fluidity of the relationship between different contexts. One of these is the Rayner’s logic of natural inclusionality. According whit Rayner’s evolutionary standpoint any living system is constantly in dialogue with its natural neighbourhood on the basis of an interdependent and co-evolutive process involved both the context and the organism. The aim of this paper is to evaluate the model proposed by Rayner in light of contextual perspective in development and educational psychology arguing as the space in between is neither a cuttable and divisible presence into discrete things, nor a mere “nothing” that could be cut off our conceptualization. Rather, it’s a ground (for a figure) in which flow and counter-flow in a fluid interplay amidst a distinct bounded context takes place.The interest for the boundary conditions calls for focusing on what happened on the border. By adopting a simultaneous perspective from two standpoints we are able to constantly focus on both aspects—what happens inside and outside different social settings—we became aware that the “walls” of the context of our living are much more permeable than has been until now theorized by psychological research.