In the historiography of post-Communist nations, historical genres such as political history and social history is more often, not discussed in the classroom, allowing for a qualitatively weak background in the social sciences as well as collective memory. For the successive generations who have completed secondary education since 1989 this is proving fertile ground for “lost” generations in Central Europe and Slovakia in particular, giving a challenge to instructors who facilitate courses and discussions on this period of history and post-Cold War political and economic developments. Moreover, for instructors from Western Europe and North American education systems, the level of standardization of instruction typical in the secondary education level is familiar to practitioners, however it is lacking in central and Eastern Europe where textbook and education reform has been undertaken in a highly charged political atmosphere. The result has been haphazard at best with political and social history after 1968 largely ignored besides a few specific events. For instruction at the university level, undertaken by expatriate lecturers, holding class discussions on subjects such as ‘shock therapy’ or ‘turncoats’ often is a lesson on the event or person instead of the intended intellectual exploration. The following paper concentrates on the challenges teaching and facilitating classroom discussions by expatriate teachers in Slovakia from the period 1998-2013 on the heritage of communism to the present political, socio-cultural, and economic system.