Agnes Smedley was an American writer, journalist, activist, and spy who traveled North America, Europe, and Asia in pursuit of her anti-imperialist and communist agendas. She came to anticolonial transnationalism through her personal and often intimate ties to India’s diasporic revolutionaries in the US (1912–1919) and Germany (1920–1929), as well as Chinese communists and Soviet spies in Shanghai (1929–1937). The chapter traces Smedley’s global crossings as a prism for exploring the power of intimacy in the making (and unmaking) of transnational solidarities, while also considering the gendered experiences of revolutionary women like her who were critical to shaping transnational anticolonialism. The chapter argues that Smedley’s most revolutionary acts were often intimate and private ones, including interracial marriage and romantic ties to leading luminaries of transnational anticolonialism during the interwar period.