This article looks at how young teens and their parents offer complex and often idiosyncratic reasons and insights into why they do or do not participate in structured activities. Young teens and their parents clearly state that the “if you build it, they will come” approach, even if it is well built, is only part of the solution for engaging young people in learning opportunities. Interviews with youth and parents explore what they are doing and what they say they want in their non-school hours. Opportunities that are flexible, less structured, and more leisure-based emerge as priorities. Although relatively content with the options currently available to them, when pressed, youth and families want more connections between people and age groups as well as more of the free-spirited, organic activities likely to emerge in neighborhoods and communities.