The goal of the present study is to examine workshops of Jewish-Israeli and Palestinian youth conducted in the post-Oslo era with the aim of promoting reconciliation and peacebuilding between the sides. The workshops were organized by an Israeli-Palestinian organization, in the framework of a peace education project. In these workshops, youth from pairs of Israeli and Palestinian high schools met for two days to discuss social, cultural and political topics. Each workshop included approximately 20 youths from each side that were led jointly by a Jewish-Israeli and a Palestinian group facilitator. The study examines four facets of these dialogue events, using both quantitative and qualitative research methods: (1) structure of activities and practices of transformative dialogue used in the encounter events; (2) attitudes and mutual stereotypes held by youth from both sides prior to the beginning of the workshops; (3) mutual perceptions and attitudes expressed by participants during the encounter; (4) effects of participation in the workshops on stereotypes held by the Jewish-Israeli and Palestinian youth (pre-post comparisons).