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This study considers well-being as a generative approach to cultivating affirming, positive learning experiences. Employing a qualitative design method, this study examines’ depictions of high and low moments in their life stories through the lens of Positive Design, Learning Experience Design, and the PERMA model of Well-Being (Seligman, 2011) to identify examples of how these constructs (positive emotions, engagement, relationships, meaning, and accomplishment) manifest and are enacted. Applying the Positive Learning Experience Design conceptualized in this study to assess the design of learning experiences illustrates opportunities to enhance experiential design with a focus on student well-being, with participant narratives revealing evidence of all five constructs and emphasizing the interconnected nature of these components and how they work together to shape experiences.