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This self-study explores what happens when best friends take on the role of critical friends in a research collaboration. Drawing on social constructionism, inquiry as stance, and critical friendship as theoretical frameworks, we examine the affordances and tensions that emerged during our work together. Using Stolle & Frambaugh-Kritzer’s Critical Friend Definition Continuum (2025) and the EASEL (Saenz, 2020) personality assessment, we investigated how our longstanding friendship and individual traits shaped feedback, reflection, and emotional dynamics. Data sources included memos, transcripts, and digital correspondence. Our findings highlight the importance of establishing norms, clarifying roles, and acknowledging personality influences. We contribute to self-study literature by extending the concept of critical friendship to include the role of personality.