My contribution to this panel considers Avi Moghrabi’s 2012 film Once I Entered a Garden to reflect on the entanglements of migration, affects, and life histories in the Levant. This example of contemporary cinema verité follows Moghrabi, the descent of Syrian-Lebanese Jews, and Mograhbi’s former Arabic teacher and longtime friend Ali Al-Azhari, a Palestinian with Israeli citizenship who, displaced from his hometown of Sufariyya in 1948, has spent much of his life living in Tel Aviv. Inspired by a pan-Levantine phonebook whose listings span geographic distances now sequestered by borders, the two document their search for locations that speak to histories made impossible by competing imperial projects and nationalisms. Utilizing ethnographic and archival research conducted in Lebanon, I pair an analysis of Moghrabi’s film with an exploration of the ways in which Lebanon’s Jewish past is critically dependent on interregional networks and histories. I first analyze how Moghrabi’s filmic exploration of the two’s everyday practices, interwoven with Super-8 letters sent between imagined Jewish Lebanese lovers separated by the Israeli-Lebanese border, shows how quotidian life can challenge the separability of peoples in the region. I then turn to my research in Bhamdoun, a Lebanese town that was formerly the refuge place of upper-class Jews from around the Levant who gathered to escape the heat of summer. Positioned in proximity to nearby hotels, villages, and a casino, the synagogue’s ruins—unkempt but structurally sound—offer a glimpse of an often-idealized past, where Jews from across the region and beyond could join the company of an intersectarian Haute Bourgeoisie by simply boarding a train. By assessing the pitfalls of a romanticized pre-imperial Levantine past, I suggest that the material traces of Bhamdoun’s yesteryears offer possibilities—and warnings—for imagining an alternative to the present geopolitical status quo of the region.