This essay discusses Gertrude Stein's literary portraits within the affective terrain of literary and cultural studies by focusing on the idea of collaboration and relationality. It attempts to configure Stein as a sensory collaborator by concentrating on the oral/aural and other nondiscursive sensory qualities such as touch that Stein insists on, specifically through repetition in her literary portraits, which have been read mostly in the context of the poet's engagement with the visual arts. I offer a new reading of Stein's writing, beyond the visual paradigm, by considering her idea of listening as a form of attention and care. Furthermore, I look at how this affective mode is realized through her approach to writing poetry as an act of "caressing" her subject matter. I argue that Stein's writing is a site for sensorial collaboration, in which new modes of relation emerge, as her literary portraits suggest the ways in which our senses implicate not only one's individual perception of the subject but various forms of sociabilities and affective connections. This essay ultimately proposes that Stein's insistence on making telling, listening, repeating, and what she calls "caressing" into a combined mode of relation evokes how poetry can become a site in which extending or transforming oneself into a collaborative mode of being becomes possible.