Learning designs that facilitate real-time, online experiential learning have, up to now, received sparse attention. This study scrutinized an online, experiential, synchronous classroom session that featured an exercise designed to highlight the dynamics of competition and collaboration, group-as-a-whole understanding, and psychodynamic processes. A naturally occurring experiential classroom experience was recorded and transcribed. This research indicates that provocative experiential learning exercises can be translated effectively to a synchronous virtual classroom environment. This research also found that group dynamic issues of competition-collaboration, establishing moral high-ground, and winning surfaced, even when group participants were interacting via small squares on a screen. This research views the issues that emerged in the study through the lens of a parallel process that reflects the issues occurring in the society at large.