This paper argues that learning for human flourishing needs a balance between small-scale, convivial experiences, imaginary and creative expression, logical, rational planning and autonomous, purposive practices. It is the second one--imaginary and creative expression--which is particularly of interest in this paper. The focus is on the capacity of playful stories around relevant learning themes to promote informal adult learning and capacity building in community settings. Informal and non-formal learning programs in community settings can often engage reluctant and wounded people for whom the learning projects--language, health care, childcare and the like--are as necessary as they are difficult. People in community settings are often embarrassed, hesitant and nervous about being singled out and shamed. In these contexts, stories of learners--even fictional ones--seem at least sometimes to be able to create a kind of softening and optimistic experience, engaging educator and learner in a playful yet insightful experience relevant to some of the actual learning projects in which people are attempting to engage.