In the pursuit of my doctoral research on the institutional history of the art department at Central Technical School (CTS) in Toronto, Canada, I amassed a collection of oral histories from 20 current and former CTS art instructors and students, recorded across the country. As an instructor in the CTS art department in addition to being its historian, I set out to produce a comprehensive and multifocal account of the history of this transgenerational community of which I am a part. The following article focuses on one research participant in particular: Sue Shintani, a former student and long-time program volunteer, whose recollections of the CTS art department helped to form an interwoven narrative of the men and women who taught at or attended this hybrid location of applied and fine art education. Sue's insights stretch over 60 years, from her experience as a high school student in the 1950s, to her time as adult student in the 1990s, to her role as a school volunteer up to the present day. In this reflective examination, I ask whether it can be claimed that the quality of oral history research correlates with the depth of the interpersonal relationship between interviewer and interviewee.