This article introduces the idea of a ‘pedagogy of regret’ to illustrate some of the inadequacies in recent government policy initiatives which target young women's drinking practices. In the Australian context, the National Binge Drinking Campaign warned young women: ‘Don't turn a night out into a nightmare’. A similar British campaign advised individualized drinkers to ‘know their limits’. The rhetorical appeal of these campaigns hinges on the notion of regret: young women will lament the excesses of hedonistic indulgence the morning after given the inevitable consequences of risky behaviour. This paper shows the limitations of such an appeal through a ‘sympathetic online cultural studies’ approach, which we use to explore the nexus between contemporary drinking cultures and the social networking site Facebook.