This chapter first examines cultural traditions that shaped the perception and experiences of the changes during the 1960s and '70s in the United States and the Netherlands. Out of the confluence of different cultural traditions, the social policies they influenced, and the different experiences of the upheavals of the unruly decades emerged what might be called an “adversarial” and an “interdependent” individualism. Using the interview material from parents who lived through these decades and began raising children in their wake, the author then unfolds the different individualisms by examining three “gray” areas parents confront as they guide their children through adolescence: the fostering of self-control, the attainment of adulthood, and the exercise of authority. Finally, we see how the individualism on which each set of parents draws sets up a logic that makes their approaches to teenage sexuality possible and plausible.