This chapter explores experiences of students in Lion’s independent day and boarding school, one of the most highly selective schools in the country, educating the children of politicians and celebrities. These young people were being taught to think carefully about e-safety and how social media could put their own and parent’s identities and resources at risk. We outline dramatic developmental differences in maturity levels in intimate social media practices between the boys and girls. Some boys were highly risk adverse and judgemental about sexting, as having the potential to jeopardise their future career prospects. In contrast some of the girls were amassing large social media followings and active across many platforms, with some girls promoting their luxury lifestyles as well as receiving unwanted dick pics and requests to send nudes. Whilst the boys were mainly worried about impacts on their careers, girls were concerned about how sexting could create problems for future committed relationships and marriage prospects. The young people complained that their sex education was completely inadequate, with some of the boys noting the wanted to learn more about digital sex issues earlier, so they would be less ‘confused’ and better prepared when things happened.