The behaviour of adolescents in our society often results in unhealthy or dangerous consequences. Professional practitioners often are ineffective in guiding our youngsters toward positive and healthy behavioural choices because they attempt to address the problem behaviours themselves, rather than the processes through which teens are motivated to make such behavioural choices. Previous research has defined "teenagerhood" as a discrete cultural stage through which many teens pass, and has suggested that their behavioural choices are often motivated by perceptions of "coolness", defined as social attractiveness. This thesis advances these notions, further suggesting they comprise a viable foundation on which to develop further research and practice in our school system, particularly with respect to preventing problems among teens. Written from the stance of an integrative-interpretive review, this paper attempts to bridge the gap between research and practice through developing an ecological overview of teenagerhood and middle-level education. This study examines a wide variety of academic and popular literature pertaining to the culture of coolness, and middle school practice. This paper draws five broad and interrelated conclusions: (a) that there is a need for innovative and appropriate research methods for integrating research and practice in education, particularly concerning ecologically complex issues such as teenagerhood, coolness, and risky behavour; (b) that the problem of youth at risk is both real and serious; (c) that many youngsters need to be cool, and adults working with young adolescents need to understand, respect, and work with that knowledge; (d) that the function and structure of schools must accommodate youngsters' real characteristics, needs, and the contextual imperatives of teenagerhood and coolness; and (e) that the roles and practices of professionals in schools must fit youngsters' real characteristics, needs, and the contextual imperatives of teenager hood and coolness.