Halide Edib's Masks or Souls?: A Play in Five Acts begins with an unlikely cast of characters: William Shakespeare, Ibn Khaldun, Tamarlane, and Nassir-eddin Hoja. Although Nassir-eddin Hoja may be less well known on the world stage than the others, his sage humor enables the synthesis of masks and souls that renders him the forebear of Shakespeare's wise fools and existential philosophers. By the end of the play, the transposition of Shakespeare into "Shake" (homonym for "Shaykh," meaning Sufi spiritual teacher) dialogically assimilates the English "Bard" into the Turkish Islamic idiom of Nassir-eddin Hoja. This essay endorses Hülya Adak's theorization of cross-cultural dialogue, particularly between the Islamic "East" and the Christian "West," as requiring "intersubjectivity" to circumvent orientalist dichotomies that have traditionally prevented understanding. Its use of this paradigm to assess Edib's Masks or Souls?, which Adak does not discuss, challenges the conclusion that Edib's engagement with the "West" in her creative works fails to exceed the boundaries set by orientalist and patriarchal discourses. The canonical and potentially colonizing Shakespeare instead reappears as an instance of the populist syncretism represented by Turkish Islam. Shake could become Shaykh in Edib's Masks or Souls?, moreover, because Shakespearean English resonated with the richly layered Turkish language Edib sought to reform but not abandon.