This narrative inquiry explores the stories and experiences of two cooperating teachers, “Journey” and “Isla.” Research puzzles being explored include wondering why educators may or may not choose to become cooperating teachers and what challenges and successes they may encounter along the way. It seeks to understand the various roles cooperating teachers must play, and explores the concept of “readiness” and what the phrase means in the context of cooperating teachers and mentorship. Support emerges as a central theme, emphasizing the relational nature of mentorship. Both participants discussed positive outcomes from their experiences as cooperating teachers, but acknowledged difficulties in supporting interns who were struggling. Questions about the pairing and assessment process arose. Both drew support from outside individuals in navigating these tensions, and both offer recommendations to consider for teachers becoming cooperating teachers and for the program as a whole. As a narrative inquiry, this research is not intended to provide a wide cross-section of perspectives, nor is it attempting to offer steadfast truths or information about program delivery. Instead, its aim is to present questions to linger with and consider as the profession moves forward in educating pre-service teachers. The intent of this study is to provide a space for voices of educators who have undertaken this necessary role in the hopes of better understanding how to support their work.