This chapter examines the shift from almost total estrangement in the early 1920s to broad enmeshment in cultural, economic, and finally diplomatic exchanges in the early 1930s. While acknowledging the importance of converging economic and strategic interests, the chapter argues that images and ideas were also significant, particularly in defining the identities and trajectories of the two countries. It illuminates the divergence between American anticommunists who loathed the atheist Soviet dictatorship and the growing number of intellectuals, journalists, African Americans, and others who became fascinated by the Soviet experiment in social and economic transformation. It also analyzes the ambivalence of Soviet writers, cartoonists, and political leaders about the United States, which they harshly criticized for its imperialism, racism, and economic exploitation, but also admired for its energy, productivity, and advanced technology. The chapter closes with a discussion of how President Franklin Roosevelt disregarded a terrible famine in Ukraine and protests by Ukrainian Americans as he negotiated for the establishment of diplomatic relations.