Coalitions and alliances are ubiquitous in humans and many other mammals, being part of the fabric of complex social systems. Field biologists and ethologists have accumulated a vast amount of data on coalition and alliance formation, while theoretical biologists have developed modelling approaches. With the accumulation of empirical data and sophisticated theory, we are now potentially able to answer a host of questions about how coalitions emerge and are maintained in a population over time, and how the psychology of this type of cooperation evolved. Progress can only be achieved, however, by effectively bridging the communication gap that currently exists between empiricists and theoreticians. In this paper, we aim to do so by asking three questions: (1) What are the primary questions addressed by theoreticians interested in coalition formation, and what are the main building blocks of their models? (2) Do empirical observations support the assumptions of current models, and if not, how can we improve this situation? (3) Has theoretical work led to a better understanding of coalition formation, and what are the most profitable lines of inquiry for the future? Our overarching goal is to promote the integration of theoretical and field biology by motivating empirical scientists to collect data on aspects of coalition formation that are currently poorly quantified and to encourage theoreticians to develop a comprehensive theory of coalition formation that is testable under real-world conditions.