Classical studies in the development of adolescents and young people emphasize both their access to hypothetic reasoning, and their identity explorations. However, as argued by Freud and Vygotsky, adolescence is also the period of life during which playing is replaced by imagination—capital in human and social development. However, how can young people imagine possible futures, in a world which is rather threatening? The arguments of this chapter are, first, that one should bring back to the fore the pleasure inherent in thinking, and second, that this pleasure may be particularly given space when thinking engages imagination. If adolescence is the age of engagement in social groups, then it may be important to consider collective cultural experience requiring imagination. In this chapter, after presenting a theoretical frame, I present the five modalities of pleasure of thinking that can be experienced in adolescence and youth, and I then demonstrate that this period is key for the development of imagination, as expansion of experience. Through a series of empirical examples, taken from the media and from research, I indicate some of the conditions by which adolescents and young people may find themselves imagining in group, and with it, enjoying their pleasures of thinking.