This article addresses the construction of "critical friendships" within the practice of one particular program evaluation. It focuses on the evolution of relationships developed during one 2-year program evaluation study that examined a collaborative educational project. Findings show that a caring interest and mentoring rapport developed between program constituents and evaluator (the author of the study). Further, this study suggests that these relationships were essential to how formative and summative feedback was used. This article suggests that the interplay between evaluator and constituents is best practiced through what House and Howe call a methodological "advocacy stance". Finally, it encourages further discourse and investigations into the ways that program evaluation is carried out in order to more thoroughly understand how relationships influence evaluation methodology and practice.