This chapter critiques current UK educational guidance on sexting, particularly a framework, which only distinguishes between “experimental” and “aggravated” sexting. This binary approach overlooks the complexity of adolescent motivations. The chapter introduces the Four Motivation Options Typology for Boys (4MOTB), a model that maps the interconnected reasons behind sexting, ranging from romance to social validation, within a developmental and safeguarding context. It argues for a shift from punitive, absolutist approaches to a curriculum-based, harm-reduction strategy that reflects real life adolescent experiences. Sexting should be addressed through relationship and sex education (RSE) that supports ethical decision-making and acknowledges teenage sexual agency. The model encourages educators to assess each sexting incident individually, balancing legal obligations with developmental understanding. Educational settings need to deliver a progressive, evidence-based curriculum that moves beyond moral panic, empowering boys to critically reflect on their actions and make informed, ethical choices in digital sexual interactions.