This chapter describes how the evolution of the adolescent society is not a simple one-way street where adolescent qualities become ever more prevalent and influential in the adult population over time. More than a decade into the new millennium there are important counter-trends, evident for some time now, that cry out for some acknowledgment and explanation. These developments are embodied in the attitudes and values of today's younger generation, a group that has been given various labels, most commonly “generation Y” or the “millennials.” A number of observers have suggested there is something quite different about today's young adults and teenagers. These new cohorts are bucking trends — undesirable trends for the most part — that had been moving steadily in the wrong direction for a great many years. The chapter contends that the “millennials” are those coming of age after the adolescent society was in full flight — roughly, those born from the late 1960s onward, the decade when adolescent norms and traits became fully manifest. In other words, millennial qualities have emerged gradually rather than abruptly, and paradoxically from within the very citadel of the adolescent society.