Background/Context: Very little empirical research has been conducted on the issue of educator sexual misconduct (ESM) in secondary settings. The few reports available typically treat a larger social issue, such as sexual harassment or child abuse; therefore, data on ESM specifically must be extrapolated. When such data are obtained, the focus has been on rates of incidence rather than the nature of the problem. Feminist scholars have theorized embodiment in education and debated whether and to what extent an eroticized pedagogy is desirable, but scant attention has been paid to how and why erotic pedagogy can go awry. Research Question/Focus of Study: A central question of this study is whether and when the sexual dynamic of teaching that many scholars believe is a condition present in most classrooms becomes ESM. This article focuses on just one step of the teacher-student affair process: how the line between "teacher" and "lover" was crossed. Participants: The primary participants are Hannah and Kim, high school English teachers who had a sexual relationship with a student. Their cases are framed with Mary Kay Letourneau and Heather Ingram, two headline-heavy teachers whose backgrounds and affair patterns are similar to Hannah's and Kim's. Research Design: This is a qualitative case study based primarily upon interviews and artifacts collected from the participants. Conclusions/Recommendations: The participants' relationships with their students was an escalation of events, a continuum upon which "crossing the line" was arbitrarily fixed at the point of their physical expression of what was already an emotional affair. The process was similar across the cases: During the teachers' attempts to save the student from academic failure, they fell in love with the students. Students initially flirted with the teachers, which the teachers did not discourage; the teachers then allowed (and sometimes created) increasingly intimate scenarios, thereby setting the stage whereby the line could be crossed, although the students initiated the physical crossing of the line. Understanding how and why teachers cross the line is more likely to be effective than the two lines of prevention and their concomitant assumptions that typically operate in schools: silence (the elephant will go away if we don't talk about it) and surveillance (instituting rules that disallow any form of touch will control outbreaks of educator sexual misconduct). In light of this study, the latter is especially ironic: A heightened emotional connection, not inappropriate physical touching, was the gateway to misconduct.