This study analyzed men’s lifestyle websites within the Pick-Up Artist (PUA) community. Employing a feminist post-structural framework, this analysis investigates how heterosexual masculinity is constructed online and aims to examine how sexual activity with multiple women is positioned as valuable to men. Four interpretive repertoires emerged: uncovering the natural —mental and physical work were required to access an authentic, natural maleness; militarization — men were rallied to defend male privilege; feminine commodities for building masculinity — women’s bodies were situated as commodities used to demonstrate achievement of masculinity; and pressured pursuit — men were urged to be the directors of sex and to overcome the obstacle of female consent. PUA authors disavowed the importance of women, though sex from women operated as a central requisite for convincingly achieving masculinity. Key tenets of neoliberalism were regularly present, where male readers were urged to decide to improve and cultivate their outward appearance, behaviours, and subjectivity.