The widespread diffusion of technology and the rise of the Internet have shaped contemporary social behaviours and processes: the resulting impacts on society are so visible and pervasive that the binding relation between humans and technologies can be read as the fundamental variable to define and characterize the last generation, called Y Generation. In fact, Y Geners show considerably different cognitive patterns and behaviours with respect to their predecessors, allowing them to multitask, affecting their learning preferences and moulding the way they use and select media to communicate. This work gives a description of Y Generation, analyzes the importance and the role technology and media played in shaping generational differences and finally attempts to find the key to extend findings to present and future work contexts.