Digital social networking (DSN) sites such as Facebook, Twitter, LinkedIn, WhatsApp, Instagram, Pinterest, among many others have garnered millions of users worldwide. It is an instance of information and communication technology that has brought about changes in the way people communicate, interact, and affected human lifestyle and psyche across the world. Some people have become addicted; some see this as beneficial, while others are skeptical about its consequences. This risk-benefit paradox of DSN flummoxes academicians and practitioners alike. This chapter discusses the social and organizational and business risks and benefits of DSN. It goes on to provide a timeline of the evolution of DSN sites, enumeration of typical characteristics of DSN sites, and a systematic comparison of offline and digital social networking. The chapter intends to serve as a cornerstone towards developing a framework for organizational strategy formulation for DSN.