This chapter inquires after the intermeshing of privilege, white male vulnerability and desirability in the narrative fantasy of the massively popular 50 Shades of Grey novel trilogy. Focusing particularly on the male protagonist Christian Grey, the chapter asks what makes the traumatised and vulnerable super-rich white man appealing as a heterosexual fantasy figure. First, the analysis addresses the use of generic romance and erotica conventions as well as the gendered forms of affective labour that the figure of the broken, rich, sad white man entails, motivates and fuels. Second, and in connection with Eva Illouz’s (2014) analysis of Fifty Shades as self-help, the interconnections of trauma and sexual fantasy within the novels’ broad appeal are examined. Third, the chapter explores how male vulnerability of the spectacular kind works in relation to social and economic privilege, the dynamics of BDSM and gendered relations of power – namely, how the narrative centrality of a privileged yet broken white man attunes the imagery of material opulence, limitless wealth, kink play and heterosexual fulfilment in a markedly depoliticised vein.