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In this essay I try to explore the relation between privacy and freedom of expression. After a brief introduction (§1) and the illustration of some examples (§2), I present some critical thoughts on the concept of privacy (§3) and I give general arguments to assert its philosophical emptiness (§4). I briefly consider the reasons for the need to affirm the value of privacy and I try to show how general arguments against the concept of privacy also apply in cases where privacy should protect freedom of expression (§5). The thesis here defended is that privacy—or, better, the propositional content of the concept of privacy—escapes philosophical analysis because it changes its reference every time, depending on the case to which it applies, without unambiguously and consistently singling out a fundamental human interest to protect. Therefore, privacy—at least in its current use—fails to provide an adequate defense of freedom of expression.