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Trans* youth (*both transsexual and transgender) comprise a new domain of “disproportionate minority representation” in juvenile legal systems across the United States. Due to an unyielding and unwarranted adherence to a binary sex/gender system, trans* youth pose a problem to juvenile legal facilities and law enforcement. This paper explores findings from interviews with 18 trans* youth who exchange sex for money and other needs in Chicago, IL, focusing on their reports of experiences with law enforcement. Being treated disrespectfully—at times brutally—and having law enforcement officers as regular “dates” were key (and conflicting) features that youth shared regarding their interactions with Chicago law enforcement in the streets.