This thesis examines Oscar Wilde's relationship to three aspects of the freighted and divisive critical debate about sexual history and sexual identity, which I describe as the gay/queer impasse. Chapter One examines the operation of this debate and the reasons for the abiding stalemate between its two sides, and it contextualises the three main subjects that I will be discussing in the succeeding chapters. The second chapter analyses Wilde's relationship to the two sets of concepts that cluster around the 'gay' and 'queer' sides of the divide, and the third explores the ways in which Wilde's conception of these concepts informs his view of how we read the history of male-male passion, desire, and relationships. The fourth and fifth chapters examine Wilde's engagement with the 'modem' and 'premodern' sexual models that were available in his lifetime: the fourth considers his perception of the emergence of the modem model and its impact on the premodern one; end the fifth explores the imposition, limitations, and possibilities of the modern model: The words 'gay' and 'queer' serve as umbrella terms to capture (1.) two different fields of concepts, (2.) two different historiographical lenses and the two forms of history that they produce, and (3.) two different types of sexual model: 'gay' refers to something more familiar, stable, modern, and locatable, and 'queer' refers to something more unfamiliar, unruly, premodern, and elusive. The thesis argues that 'gayness' and 'queerness' are equally present in Wilde's oeuvre in the three aforementioned contexts, and this argument goes against the recent critical trend of underplaying, problematising, or even effacing the' gay' components of Wilde and his texts. A key part of my argument is that the 'gay' and 'queer' elements in Wilde's oeuvre are best understood in relation to a complex dynamic of interplay and interchange between them.