This dissertation scrutinizes expressivist theories of first-person privilege with the aim of arriving at, first, a handful of suggestions about how a `best version' of expressivism about privilege will have to look, and second, a critical understanding of what such an approach's strengths and weaknesses will be. Roughly, expressivist approaches to the problem of privilege are characterized, first, by their emphasis on the likenesses between privileged mental state self-ascriptions and natural behavioral expressions of mentality, and second, by their insistence that an acknowledgment of these likenesses is required in order properly to understand the characteristically singular privilege with which one speaks of one's own mental states. The dissertation proceeds in five chapters whose individual tasks are as follows: The first chapter sets out the definition of the phenomena of "first-person privilege" in use throughout the dissertation and defends the claim that those phenomena are indeed real and so the philosophical problem of accounting for them is indeed serious. However, there is no presupposition made against the possibility of an expressivist account of the phenomena of first-person privilege. The second chapter sets out the basic motivations informing expressivist approaches to the problem of first-person privilege. Four immediate and significant questions for the expressivist approach are set out. The chapter also considers one `simple' way of responding to those questions and set outs the most pressing difficulties for a `simple expressivism'. The third chapter sets out my view of Wittgenstein as a methodically non-theorizing philosopher, criticizes rival views and, finally, sets out my view of the Wittgensteinian responses to the four questions set out in chapter two, given my view of him as a philosophical non-theorizer. Many of the later suggestions about a `best version' of expressivism draw directly on my best understanding of Wittgenstein's own approach to the problem of first-person privilege. The fourth chapter sets out David Finkelstein's, Peter Hacker's and Dorit Bar-On's responses to the quartet of questions for expressivists about first-person privilege, while flagging a number concerns for each author's approach. The final chapter condenses and reviews the concerns already raised for the expressivist approaches already canvassed and makes a number of suggestions about the most viable expressivist options for dealing with them. With that in place, the last chapter proceeds to comment on the overall plausibility of the sketch of a `best-version' of expressivism that emerges. Also, concerns to do with the relationship between expressivism about first-person privilege, epistemological foundationalism, content externalism and the mind-body problem are discussed.