This paper follows one small, Christian university's five-year experience with student charity date auctions. The contemporary re-emergence of date auctions represents a backlash against gender and racial progress. Student leaders believe that in a post-racial and post-sexist society, race and gender are decontextualised neutral elements of identity. Students see their expressions of racist or sexist practices as quaint or ironic, as markers that they have sufficient cultural capital to reference historical events or practices. This perceived mastery of cultural signs is what marks these expressions as hipster racism and sexism. The date auction is difficult to unpack and challenge as it rests on privilege blindness, individualism, and the powerful rhetoric of irony. Using a close reading of the student newspaper, we analyse the discourse surrounding the date auction revealing the maintenance of patriarchy and white supremacy within the academy.