Can we philosophize Twitter ? Is 140 characters enough to cultivate a virtual community based on representative communication and the sharing of opinions ? The present article seeks to address these questions through the analysis of two studies conducted on Twitter by the author. The objective is not only to highlight Twitter’s potentialities and limits, which are already partly known, but also to confirm the possibility of philosophical investigation as it pertains to the era in which it emerges and to the tools through which it is expressed. It is a question of understanding these times and these tools, to relinquish the acquiescence of common sense and its categorizations, to exercise the right to critique, which philosophy has always upheld, particularly when faced with that which may seem inevitable. In return, it is a question of understanding what philosophy can be today, in an era of new technologies, to ask oneself what philosophizing means with regards to and through these new technologies, and especially to explain how it is possible to truly philosophize, in a just and good way.