While the influence of Virginia Woolf’s writing on Eudora Welty’s fiction has been touched upon briefly, and occasionally fully examined, by several critics, no critical attention has been drawn to the two writers’ highly similar creation of outsider characters. This essay proposes that Welty’s portrayal of Miss Eckhart in her short story cycle The Golden Apples (1949) can be read as a response to Woolf’s depiction of Miss Kilman in Mrs Dalloway (1925). Both characters are depicted as German spinster tutors who have an intense homoerotic desire for their pupils and are ostracized by society. Against the backdrop of the early 1920s, both texts let us take a glance at how an interwar society marginalizes an outsider in tandem with the rise of anti-German sentiment in England and the United States. Particularly, by comparing the two characters’ outsiderness marked by their class, gender, sexuality, physicality, and ethnicity/nationality, this essay attempts to show how the two writers’ treatment of them helps us configure the ways in which space intervenes in the (re)production of individual identities. While Miss Kilman’s shopping excursion designates her as a lesbian flaneur and epitomizes the department store’s function as a heterosexing, pseudo-public space, Miss Eckhart’s piano recital represents her agency as an artist who works to transform domestic space into an alternative public sphere for children and women in a small town in rural Mississippi. A kinship between Woolf and Welty established through their similar characters encourages us not only to interrogate the position of outsiderness predicated upon the dialectics between difference and sameness, but to problematize normative, exclusive, and heterogeneous locales functioning in society.