This chapter explores how organizations, groups and individuals using the Internet are continuously and routinely engaged in negotiating the boundaries between real and virtual time-space. With the contemporary fullness of online life still effectively in its teenage years, the chapter attempts to highlight some key points of interest with regard to humor studies and the present digital age. The first era of the World Wide Web, now called Web 1.0, refers to the capabilities of static web pages and the ability to access them from individual computers. Current scholarly attention to online and digital culture tends to characterize as "old media" any technologies prior to the digital age, which from a humor perspective might include anything from the satirical pamphlet to the political cartoon, film, and television comedy. It has been suggested that the networked architecture of the Internet replicates human structures both bodily and socially. Day-to-day Internet engagement reveals further expression of humor support.