Current knowledge about adolescent development (drawing primarily from developmental pediatrics and psychology) is reviewed to determine whether research and theory can help deepen understanding of why high school continues to be an alienating experience for large numbers of students, and this question is examined through responses of high school students to questions relating to student engagement. Sophomores and seniors (n=178) in regular and honors classes at nonurban high schools in Florida were interviewed in depth for the study. Chief among the findings is that adolescents do not sharply distinguish between intellectual and emotional matters; difficulties in grasping the content of courses are not separated from feelings they have formed about their teachers' personalities. They make an effort to engage when they feel that their teachers care about them personally. Their most poignant complaints have to do with the ways schools prevent opportunities for socializing. Many school structures and policies act in ways counter to the adolescent's needs and serve to reduce student engagement. Mismatches in the school experiences of adolescents are described. To increase the commitment and affiliation of high school students the notion of engagement needs to be expanded to include values and desires indigenous to adolescents. (Contains 36 references.) (SLD)