Currently, there is much excitement about Web 2.0 as a novel platform for experiencing, producing, and consuming leisure, particularly through social network sites. On the other hand, there are skeptics who sound the alarm on these spaces, viewing them as diluting of human relations. The perspective that guides this paper is invested in neither a utopian or dystopian posture but sees historical continuity, pointing out that performing leisure is a basic human impulse that has also found expression over the centuries. With regard to the online sites used for leisure, it makes the case that the history of the development of the public park, product of a complex interplay of interests and agendas of different stakeholders, provides a particularly rich resource for gaining insights into the evolution of social networking sites. To illustrate this heuristic potential, it draws on experiences ranging from democratization of Beijing’s parks in early twentieth century to the movement of flâneurs across Parisian public spaces to comment on the architecture of and activities on social network sites.