This article analyzes the meaning of alcohol in relation to young people’s sexuality, with focus on acquaintance rape. Drinking is a way to stage oneself as mature; it is intentionally used by both male and female youth to make sexual pleasure possible. It is argued that in the context of sexuality among young people, there is a fine line between freedom and gender-specific restrictions. The research on acquaintance rape and alcohol drinking among the youth is traditionally dominated by the concept of risk. This article introduces the concept of chance, along with risk, to grasp the complexities of the grey zone situations of acquaintance rape among the youth. The risk of social stigma within the gender game increases with drinking alcohol simultaneously as the chances of expanding the limitations of gender roles also increase with drinking. These social stigmas, embedded in the gender roles, are central to understanding when a pleasurable situation turns into an acquaintance rape. The article is based on 95 police reports of rape and 37 focus groups on alcohol and sexuality of the Danish youth. The analysis takes it onset in a single case.