The purpose of this study was to explore female varsity athletes’ perceptions of how they developed high levels of dispositional optimism in sport. Eighty-three female varsity athletes completed a domain-specific version of the Life Orientation Test (LOT: Scheier & Carver, 1985). Nine participants (M age = 19.33 years, SD = 1.5) who had high dispositional optimism in sport then completed individual semistructured interviews. Interpretive Phenomenological Analysis methodology was used. Results showed that during childhood, participants perceived that their parents were supportive, provided feedback, and allowed them to have choice over the sports they played. During adolescence, coaches began to play an important role and participants were also able to learn about being optimistic through the positive and negative experiences they encountered. During early adulthood, participants developed personal narratives about the ways in which they approached sport with optimism.