This chapter presents findings from Swans School for Girls, a former grammar school, now a ‘single sex’ girls’ comprehensive, located in an affluent London borough. Given there are no boys at the school until sixth form, the online environment became very important for connecting with romantic interests. At Swans we got a bird’s eye view into how the girls were creating sexualised identities online and their digital dating rituals with peers in their social media networks. They commented at length on the digital identity performances of boys who create and send provocative images, oftentimes to harass girls. We also explore several episodes of image based sexual abuse that have happened to girls at the school. A mixed genders group of older teens in sixth form explained how out of touch their anti-sexting education was, noting they have been repeatedly shown out of date videos, and told not to produce child pornography but had never been taught anything about image-based sexual harassment and abuse, including no guidance or support on LGBTQ bullying, harm and violence. We show how single sex schooling creates contexts of isolation from real life friendships and relationships with differing genders, creating even more impetus for digital sexual relationships than in mixed gender schools, hence a need for strong digital sex education in these sites.