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Laws governing adolescent sexuality are incoherent and chaotically enforced, and legal scholarship on the subject neither addresses nor remedies adolescents’ vulnerability in sexual encounters. To posit a meaningful relationship between the criminal law and adolescent sexual encounters, one must examine what we know about adolescent sexuality from both the academic literature and the adults who control the criminal justice response to such interactions. This article presents an in-depth study of In re John Z., a 2003 rape prosecution involving two seventeen-year-olds. Using this case, I explore the implications of the prosecution by interviewing a variety of experts and analyzing the contemporary literature on sexual norms among youth. I also relate a series of interviews conducted with the major players in the prosecution. Examining this case from a variety of perspectives permits a deeper understanding of how the law regulates adolescent sexual encounters and why it fails.