The latest theorizations about generations try to explain the concept as a multi dimensional issue (Donati 2007) through the assumption of a common life experience, shared by the mem- bers, and the emergence of that specific generation as a social-fact itself. The concept of generation then assumes reflexivity process (Giddens 1991) both at an individual and at a collective level. Edmunds (2005) proposed that mass media could be a common landscape able to offer a world-wide shared stage for "concrete historical problems". If the generational ‘we sense’ can be described as a meaningful set of connected criteria for interpreting and articulating topics in communication, then mass media would be the place where those ‘criteria’ are learnt. Recent evolution of media technologies and the rising case of the so called web 2.0 add an interesting element to the described scenario. While the Mass Media system could have been identified as the place where the generational we sense was constructed, what does it happen today in a media environment where every user can add content (User Generated Content) that is often visible to a lot of unknown spectators? Where do we learn the connected criteria for interpreting and articulating topics? The paper aims to investigate this specific and furtive phenomenon, proposing an innovative methodological approach of analysis of online User Generated Content: blog entries.