The current qualitative study draws on Larson’s theory of positive youth development and on concepts from Self-Determination Theory to postulate that program participants will derive a sense of enjoyment and challenge in program activities when they perceive that the program supports their psychological needs for competence, autonomy, and relatedness. Self-determination theory suggests that when programs support participants’ need for autonomy, competence, and relatedness, the participants will in turn experience a higher sense of motivation and engagement within the program. The emergent themes found from the thematic analysis helped to support this theory by suggesting that Cool Girls participants experience a sense of engagement and motivation through program activities that promote autonomy/independence and peer/adult connections. Further, possible variations in perceived needs fulfillment across age groups were explored.