This chapter explores the motivational factors behind teenage boys’ participation in technologically mediated sexual interactions, particularly active sexting. It identifies four key motivations: sexual desire, perception of body image, social belonging, and aggravated sexting. Sexual motivations such as flirting, arousal, and passion accounted for the majority of sexting, while smaller groupings were linked to body image and attractiveness, sexting to gain social acceptance, and a very small proportion involved aggravated sexting with safeguarding concerns. The chapter highlights that motivations around body image are often rooted in subjective self-judgment rather than behavioural intent. Some participants expressed moral or ethical objections to sexting, often influenced by religious beliefs or negative past experiences. Understanding the underlying reasons for sexting is more effective for educators and practitioners than focusing solely on punitive responses. Addressing the “why” behind the behaviour is essential for developing meaningful interventions and supporting healthy adolescent development.