This paper describes a self-study of two collaborations. The first collaboration focused on an attempt to study the teaching of social justice issues to pre-service student teachers. The second collaboration was an attempt to understand why the first collaboration was only partially successful. The study charts the process of collaboration over two years. The methodology is highly reflective, depending primarily on sources that were seen as being significant in retrospect rather than collected with a sense of purpose. Data include emails, conversations noted at the time or remembered, notes made of discussions at conference presentations, and reflective journal entries. Conclusions are drawn with significance beyond this self-study. They include clarification of the nature of collaboration and the parts played by the role and personality of the collaborators, factors to be taken into account for success, reasons for collaboration, and the importance of focusing on the self who is inviting or persuading others to collaborate rather than on anyone else. Presented as a narrative in dialogic form, the paper demonstrates the growth of understanding over the period of the self-study and illustrates the development of one kind of collaboration among congenial colleagues.