When is sexting not sexting? How do producers and sharers of naked and seminaked selfies negotiate and engage with broader cultural codes and conventions of sexed and gendered self- representation? This article draws on interviews conducted in 2012 with three mixed-sex groups of 16- and 17-year-olds in Sydney, Australia, as part of the Young People and Sexting in Australia project (Albury, Crawford, Byron, & Mathews, 2013). It focuses not on the images that might most easily be categorized as “sexts” (i.e., images intended to be exchanged within flirtations and intimate relationships) but on other, more ambiguous images, defined by participants as private selfies, public selfies, and a subgenre of joke selfies known as sneaky hats. These images were not discussed in all groups, but when they were, they provoked lively debates in which participants explicitly and implicitly explored complex and at times contradictory understandings of the interplay of sexuality, gender, and representation. While not representative of all young people’s experiences of digital-picture-sharing cultures, these discussions point to a significant gap between young people’s own interpretations of their ordinary or everyday digital practices and adults’ interpretations of these practices.