Young people today, and in particular young women, report increasing levels of stress, eating disorders, feeling of depression and dissatisfaction with their bodies. This scenario comes from a generation and class of young women who have never had so many chances in life – both in regard to education, careers and personal life – and who are doing very well. This chapter discusses this paradox in a generational perspective, conceiving the body in a broader context of age, relationships, development and agency. By analysing how young women and men’s feelings about their bodies have changed over three generations, the chapter explores the relationship between subjectivity, bodily pleasure and concern and how this may reflect and express the changing social conditions for the development of gender identity, autonomy and intimacy. In the concluding section, I will discuss what further transformations of bodily and psychosocial shifts we might see in young people today – representing the ‘fourth generation’ in relation to my study.