This chapter seeks to unravel a number of the conceptual regularities that underpin approaches to masculinity and, in doing so, unpacks the conceptual basis of what the authors understand as masculinity. It develops these points to deconstruct the concept of masculinity itself. Masculine subjectivity is discursively constituted through the conceptual centrality of masculinity. The chapter uses the case of dogging to re-think the nature of men's subjectivity and question the usefulness of masculinity. Often, 'dogging' is described as a form of cruising for straight people and has its history within the space of the 'lovers' lane'. Masculine subjectivities are conventionally anchored through the four 'H' concepts. Importantly, such concepts have a number of regularities that position masculinity in a number of ways. One of the responses of the men to experiencing feelings of inadequacy was to compensate by adopting the style of a jock or by having an extra-marital affair.