This autoethnographic paper explores the complex and often contradictory impulses experienced by a former pulpit rabbi around interreligious dialogue. It examines the tension between the desire to protect one's community external approaches and the simultaneous yearning to foster understanding, respect, and even mutual learning through interreligious encounters. The paper will delve into the Orthodox Jewish hesitancy towards public theology and interreligious engagement, rooted in historical concerns about assimilation. This hesitancy is often fueled by interpretations of scripture, such as Balaam's prophecy ("a people that dwells alone"), a historical memory of persecution and forced conversions, and fears that one's congregants are not grounded enough in their own traditions to encounter others. The paper will then juxtapose this protective instinct with the author's own motivations for engaging in interreligious work. These motivations include the desire to illuminate the richness of Judaism, correct misperceptions, cultivate greater interreligious understanding and acceptance within both the Jewish community and wider society, and to better learn one's own tradition by seeing it in the light of the interreligious dialogue. By analyzing these internal conflicts, the paper aims to shed light on the challenges faced by religious leaders in navigating the delicate balance between communal preservation and interreligious engagement. Ultimately, it argues that understanding and overcoming these obstacles is needed to unlock the transformative potential of interreligious encounters for individuals and communities. The paper will also touch upon the varying approaches within Modern Orthodox Judaism, where some permit social and political contact while drawing a firm line against theological dialogue. The presenter is now an associate professor at the University of Southeastern Norway and a senior research fellow at the Ohr Torah Interfaith Center.