By examining the little used notes and essays of Paul Siu produced in the 1930s, we find evidence that challenges early images of unassimilable Chinese men and enslaved Chinese women. In early twentieth century Chicago, racial categories for Chinese men were rigid. However, their categorical foreignness did not prevent Chinese men from establishing or buying sexual and/or emotional relationships with white, black, and mixed-race women. The prevalence of these relationships reveals the ways in which the image of the unassimilable eternally foreign Chinese man collapses when interrogating individual intimate relationships. For Chinese women, I argue that within the popular discourse of “white slavery,” the racial category of whiteness became contingent on the conditions of their gender and allowed for Chinese women to be enfolded into whiteness. Prostitution allowed Chinese women to gain some economic freedom while they escaped the harsh conditions of servitude and was a central avenue for Chinese men to form intimate relationships with local women.