Teaching the topic of a country’s borders can be challenging. This is especially the case in Israel, where not all the state’s borders are agreed: there are internal disagreements between parties on the ground and external disagreements between parts of the international community and the State of Israel. A border, the very symbol of stability and consistency, contains mixed and contradictory aspects; the borders are not always well defined and, for many people, sensitive and contentious subjects. Therefore, teachers often avoid or feel uncomfortable teaching the topic, even though they know well its importance. This study examines existing curricula and textbooks used to teach the topic in Israeli high schools, and develops a picture of teachers’ perceptions of teaching the topic through qualitative research. On this basis, the paper proposes a training model that addresses both the social and emotional side of the subject and the historical and political knowledge required to teach it. The purpose of the model is to better equip and enrich teachers to take on the task while minimizing fear of encountering or provoking adverse reactions. The teacher’s role is to expose students to different perspectives and positions, so students can begin to assess the problematic and complex nature of the topic in general and Israel’s borders in particular.