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The divide between the various levels of education in Latin and the field of Classics can be seen most clearly in the discrepancies between adolescent Latin (7-12), college and post college instruction and programs. There is no lack of enthusiasm from students or teachers, yet there is a conflict between expectations and acquired skills. With inadequate training and paucity of experiences, graduate students will lack preparation for teaching or becoming scholars in the field. In this paper, the author will discuss the experiences needed for adolescent Latin students and graduate level students as they embark on their own journey through Latin and Classical studies. Adolescent students need to find their heart-shaped piece (Teaching Latin, Teaching Kids, Ancona 2006) which hopefully gives them the desire to pursue Latin and the field of Classics. For adolescent students, connection to selected texts, classmates, and teachers will be integral for continued learning. College and graduate students will need tools for professional development, classroom management, and the ability to be continually flexible and creative. There is also a need for an increased exposure and exploration of the history and application of various pedagogical approaches. As the current state of Latin education is shaky, it will become increasingly necessary to revisit the importance of Latin and its ability to enhance other subject areas. Therefore interdisciplinary work must be explored within a World Language department and the school as a whole at the secondary level. The author will discuss experiences as both a graduate student in a teacher-preparation program, and simultaneously, a public school Latin teacher. In light of the divide between various levels of Latin education, the author will compare and contrast the past experiences of learning Latin at the secondary level, college level and post graduate level.