Whereas social network sites and media-sharing sites such as Facebook, Instagram, and YouTube take up a large part of many teenagers’ lives more rapid and elusive modes of online communication are playing an increasing role in managing teenagers’ daily communicative routines. In particular the visual messaging app SnapChat has taken over much of the social interaction between teenagers in a Danish context. Introduced to the international market in 2012, the use of SnapChat has increased rapidly in Denmark within the past year. Frequent users report to send more than hundred visual messages a day. SnapChat works as a swift visual channel where personal messages are deleted within few seconds or at the latest within 24 hours depending on how the sender chooses to time her message. This ephemeral frame allows for new ways of displaying self-presentation that are not permanent and lasting as other social media. Due to its relative newness only limited research has been concerned with SnapChat as a mode of communication and such literature is primarily focused on the issues of ethics and technology rather than the social workings of the communicative dynamic (e.g. Bayer et al. 2015, Poltasch 2012). This paper discusses the use of SnapChat embedded in its ethnographic context as a mode of communication that ties into larger social dynamics of teenagers’ quotidian practices. Based on extensive fieldwork among teenagers at the age of 14-15 in a school in rural Denmark this paper discusses the transgressive potential of SnapChat. Data consist in a large collection of the visual messages of teenagers in two classes gathered over a period of five months. Additional data was gathered through interviews about media ideologies (Gershon 2010). In the teenagers meta-talk about SnapChat the app was framed as a platform that made room for ugliness – a platform that even required some sort of hideousness whereas Instagram in comparison required the opposite – pretty photos portraying the teenagers as good looking. In the paper we discuss such meta-commentaries about required ugliness and compare them to collections of the teenagers’ SnapChat interaction. In the teenagers’ life at school romantic and sexual desirousness plays a crucial role in gaining social value in the peer group (Holland and Eisenhart 1992). The ideology of required ugliness makes it possible for the teenagers to disobey such macro norms of attractiveness in the heterosexual marketplace (Eckert 2009). However, the ugliness that is constructed within the frames of SnapChat has its own set of aesthetic rules. The ugliness is a chosen ugliness that is performed in elusive moments – an ugliness that disappears shortly after it’s constituted. The defining principle of the constructed ugliness is removability and disappearance. Thus being ugly in this context is not a contrast to oppressive macro norms of perfected bodies and beauty (Neely 2012), but rather complexly entrenched in such norms themselves. The ugliness is momentary, a matter of self-display put on top of a more lasting and continuous demand for beauty. Hence, this alternative set of aesthetics both appear to transgress and reinforce gendered and sexual norms in teenage life.