This chapter illustrates that an emerging geopolitical clash of interests in the Far East and competition on the world grain and oil markets during the last two decades of the nineteenth century were softened by the active development of trade, economic, and technological collaboration, as well as by the alluring prospect of Americans gaining access to Russia’s Asian market. On the one hand, the American reaction to anti-Jewish pogroms in the Russian Empire, repressions against fighters for Russian freedom there, and mass emigration of ethnic and religious minorities to the United States turned Russia into an object of America’s mission to liberalize the world and stimulated the erosion of the Russia–US “historical friendship.” On the other, America’s philanthropic movement during the Russian famine of 1891–1892 and Russian participation in the Chicago World’s Fair of 1893 manifested this friendship. While focusing on Russians and Americans discovering each other on a large scale, this chapter emphasizes that contradictions in their mutual perceptions stemmed from domestic developments in each country, leading to their becoming mutual constitutive Others.