Using a grounded theory research design, this paper examined the collaborative learning experiences of secondary school students in Singapore. The core phenomenon that emerged was the need for social interactions in collaborative learning, both in classroom and online settings. Educators often take for granted that effective collaborative learning will occur naturally once students are assigned to work in groups. In examining students’ dissatisfaction when working in groups, this study highlighted the importance of surfacing these hidden assumptions for careful scrutiny. The key factors identified were centered on the need to address social challenges within collaborative learning. These included a pragmatic, results-oriented approach with limited interpersonal engagement used by students that can compromise collaborative learning outcomes. Having a deeper understanding of the challenges that resulted from limited social interactions provides educators with insights when designing classroom and online learning activities. This paper contributes to the understanding of groups’ active learning to inform pedagogical practices for educators engaged in designing better collaborative learning experiences. Educators and curriculum designers need to be aware of the social drawbacks in collaborative learning in order to design a more socially engaging learning environment.