Learning to Play with the Machines will increase visibility, scholarship, and communication between the fields of political and computer science. The project is organized around three major themes: Dialogue, Discovery, and Design. The centerpiece of the Dialogue theme is a roundtable discussion series which will engage experts in both political and computational science from multiple universities across the United States. Participants will discuss the commonalities, divergences, and hopes for the two fields, tackling difficult topics such as the limits of automatic analysis and applications of big data. The Discovery component includes two interdisciplinary case studies which will push the frontier of natural language processing in political science. One investigates changes in Hong Kong’s press freedom, and the other will investigate the signaling and legacy effects of the Beijing Olympic Games. These studies will create mentorship and student co-authorship opportunities to grow the next generation of computation-forward political scientists. Ideas emerging from the roundtable discussions and the case studies will inform the Design of a methodological framework that will responsibly integrate computer science techniques into social science research questions. This project will spark informed discussions around complex topics, redirect research agendas, and nurture a new generation of scholars with cross-disciplinary talents.