In this paper, originally presented as the Presidential Address at the 6th Biennial Conference of the International Academy for Intercultural Research, the author attempts to explain an intercultural conundrum suggesting that young people may be more sophisticated in terms of intercultural sensitivity than their teachers. The paper examines the intersection of four interrelated areas as they pertain to education and the development of intercultural sensitivity – intercultural content knowledge, intercultural pedagogical knowledge, intercultural experience, and intercultural applications of technology. Each of these influences, all coming together in the lives of young people in ways never before encountered, offers insights into the different life experiences encountered by students and their teachers. Areas of further intercultural research and possible policy implications for educators are considered.