Many organizations are trying to mimic the successes of companies like Google by emulating their work culture; a culture of playfulness, flexibility, and diversity. Organizations not only have created modern environmental designs, but also have employed playful people, encouraging them to toy with new ideas in ways that they become the innovations of tomorrow. In fact, organizations are now bringing in experts to help teach and guide employees to become more playful, improvisational, and cohesive in their collaborations with each other. Often, these experts come from the world of improvisational theater. This study aims to understand the process by which adults develop and maintain this playful style of collaboration. By participating and observing a new, practicing, improvisational comedy team, I investigated the ways that the team got to know each other, improvised, and collaborated. This ethnography observes the team as they discover the dynamics of play, while also investigating the forms of communication facilitating or inhibiting play. The rich data gathered over a four-month observation period revealed three major phases of group play development: a yielding/matching phase, a posturing phase, and a predicting and teasing phase. The overall finding of this project is that the understanding of group play should not be describe a collective state, but as a series of initiating relationships. In addition, a spectrum of support/competitiveness emerged as a tool for qualifying play. Implications for these findings are discussed. Keywords: Play, Improvisation, Collaboration, and Cohesion