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This qualitative self-study contributes to the self-study field, while building on chatbot utility trends, asking: Can artificial intelligence (AI) serve as our critical friend in self-study? Our theoretical frame includes Thought Collective and More Knowledgeable Other. We compared critical friend feedback from a previous study and AI feedback to the same dialogue. Data sources included: (1) original dialogue journals; (2) AI generated responses to these dialogue journals, and (3) transcripts from our conversations. To analyze, we used direct content analysis and real-time dialogue. Findings indicated AI can act as a critical friend by listening and probing, but fell short in critiquing. More research is needed to understand AI as a critical friend and/or supplement to this research tool.