This article explores interactions with difference, highlighting what I call the “generosity paradox,” a term that refers to how we suspend disbelief and certainty in favor of a constructed potentiality not limited by preexistent knowledge or categories of authenticity and legitimacy. Touching on overlapping concepts from rhetoric, philosophy, gender studies, disability studies, and queer theory, the discussion explicates fictional encounters with radical alterity in the film Her (Spike Jonze, 2013) to show that attempted respite from frustrating, confusing, and frightening interactions limits our voice, undermines difference, and favors a unifying persuasive intent, which more likely than not involves an attempt to change Others rather than allowing our mutual differences to generatively remain.