This article is a theoretical, experiential and reflective analysis of potential problems that may arise when teaching cohorts of students. Although more often than not teaching cohorts of students can be a fulfilling experience, the authors have, on occasion, taught cohort groups that were challenging. The authors speculate whether this generation of students is really different than previous generations and believe that was is more relevant than making intergenerational comparisons when encountering cohorts of students is the literature on group development. In addition to reporting on the literature of stages of group development, they also examine how the group defines membership; how it creates communication and role structures; and how to deal with influential high-power students. They also examine how the concepts of transference and deindividuation may apply to the cohort group and suggest that the classroom can be an important venue for personal development.