The chapter explores US–Russia relations in the years before Russia entered her second revolution in February 1917 and America joined the First World War in April 1917. This period was complicated by discrimination against Jews and other ethnic minorities in Russia, by ideological differences between American democracy and Russian autocracy, and by geopolitical disagreements. Yet these elements of conflict did not hamper the two states’ rapprochement, which began at the end of 1914 and at times resembled the euphoria of a honeymoon. This chapter emphasizes that the surprising thaw in US–Russia relations cannot be explained only by the convergence of the two governments’ interests: namely, that the Russian Empire desperately needed to buy American supplies for its armed forces, while Americans were eager to sell their surplus products. Interactions between Imperial Russia and the United States call for more comprehensive consideration, with a particular focus on the changes in mutual representations and the intensified process of Russians and Americans studying each other. This is precisely what this chapter sets out to provide.