In May 1830, the Protestant missionaries of the American Board of Commissioners for Foreign Missions (the ABCFM), returned to Beirut after a two-year sojourn on Malta. In order to revived their new social-religious community in late Ottoman Syria, the mission sought to establish a central space to base their work. Being foreigners and unable to rent property directly, they chose an unusual rental agent: the widowed, teenage convert, Susan (Sardis) Wortabet. The aim of my paper is to analyze Susan’s story and her “very peculiar trials” as a case study of gender and sexuality within the entangled histories of late Ottoman Syria. Many studies of missions focus on the “winners” or successful converts (religious or cultural), whose accomplishments are commemorated. In contrast, those applying structuralist views, such as the theories of Pierre Bourdieu, argue that cross-cultural encounters ruptured individuals’ identities, particularly those on the receiving end of missions, making them “mis-matched” to their indigenous society. More recently however, scholars have analyzed missions and colonial encounters as complex sites of both empowerment and marginalization, for which the new message was selectively received, appropriated, and/or rejected by the local communities. The aim of my study is to continue this recent trend by analyzing the ways that a specific cross-cultural encounter entwined with a functioning culture to provide both opportunities and hurdles for an individual. This will be done through an intersectional analysis of Susan Wortabet’s identity. At various points in her life in Sidon and Beirut, different elements of Susan’s identity were emphasized—in some instances offering her privilege, but mostly disempowerment. Tracing Susan’s “very peculiar trials” will not only illuminate a hitherto marginalized history, but it will also open up questions onto the construction of gender and sexuality (and their affiliated hierarchies) within cross-cultural encounters and the use of interdisciplinary theories and methodologies to investigate them. Is it possible to identify the terms for an intersectional analysis within a dynamic and ever-changing social space? How does one research a historical “matrix of domination” as experienced by the marginalized who left very few sources? What are the drawbacks and benefits of adapting intersectionality, a successful theoretical tool for feminist analysis within the social sciences, to the analysis of an entangled history?