Worrying about privacy is a growth industry. The public is highly concerned about how its personal information is collected, stored, and processed. Technology companies compete to create new applications that will analyze personal data and meet new needs, such as the ability to broadcast one’s GPS data to family and friends (no more lunches alone). The government is interested in access to personal data for law enforcement, regulatory, and administrative purposes. And the media, when not reporting on the latest privacy invasions by companies or government, is publishing “tell-all” stories on anyone viewed as newsworthy, that is, deemed worthy of its attention. Two excellent guides to this cauldron of law, social change, and technology have now been published. These are Lawrence Friedman’s Guarding Life’s Dark Secrets, and Daniel Solove’s The Future of Reputation. In this Review, I discuss and analyze the main arguments of both books. Friedman and Solove make major contributions to our understanding of privacy law. The great benefit of Friedman’s work comes from its rich depiction of the legal and social context of privacy in the nineteenth and twentieth centuries and the uncertain fate of it in the twenty-first century. The merit of Solove’s work is his precise guidance through the new landscape of Internet-based phenomena and his insights into how these affect privacy and reputation - often in a fashion unanticipated by the general public. I also offer critiques of each volume. Regarding Guarding Life’s Dark Secrets, I argue that Friedman’s terminology regarding social structure is looser than it should be, which leads to a sacrifice of some intellectual clarity in the otherwise brilliant landscape of his book. Moreover, Friedman warns that in the future, technology will work as a way to squeeze discretion and privacy out of the legal system. In my view, however, technology is today accompanied by a series of discretionary choices that affect privacy. Technology provides new and complex ways to disguise discretion. In The Future of Reputation, Solove is interested in how norms can affect behavior and even supplement law. I would have liked to have heard more from him, however, about how cyberspace affects the generation of norms, and how his privacy-promotive norms are to be generated. Moreover, Solove largely views law as an independent variable. He approaches law as a norm entrepreneur and calls for a number of changes in it. Yet, in certain instances, I wished his proposals to be more detailed and more fully operationalized. Finally, I suggest a number of new Internet-based phenomena that Solove might consider in the future, perhaps in Reputation 2.0, the (hypothetical) next edition of his book.