The growing popularity of social networking sites such as Facebook or Twitter has made a strong impact on the workplace. This essay provides insight into the nature of these relatively new, digital channels of communication as well as the socio-legal environment they function in. How does the presence of social media shape the dynamics of the employment relationship? Can a routine pre-interview Google search lead to discriminatory selection practice? Can negative comments posted online about the management serve as grounds for disciplinary action, including termination? We follow the parties to the employment relationship as they use or abuse the opportunities offered to them by social networking sites; and examine how the employees’ right to privacy and equal treatment is balanced against the employers’ lawful rights and interests. In search of key patterns as well as potential answers, cases from different countries in and outside of the European Union are studied.