This thesis contributes to the literature on intergroup contact by exploring the long-term impact of grassroots efforts on members of majority and minority groups involved in an intractable conflict. In such circumstances, the conflict parties’ existential survival is perceived to be at stake, which results in salient group boundaries magnified by competing memories of collective trauma. Drawing empirical support from the Jerusalem Youth Chorus—an Israeli-Palestinian encounter program based in Jerusalem—this paper examines opportunities to desecuritize intergroup relationships from the bottom-up. To this purpose, it scrutinizes Gordon Allport’s Contact Hypothesis and narratives of historical trauma. The findings from 16 semi-structured interviews conducted with alumni participants provide unique insights into the impact of a hybrid approach to contact, with music and dialogue providing fertile ground for sustainably rethinking us-them relations toward greater boundary permeability. They also highlight the scope and the limits of conducting bottom-up “memory work” in a societal context of severe asymmetry. Group-specific results are highlighted.