Building age-friendly communities is a global as well as a national concern. The purpose of this paper is to explore fundamental tensions underlying the formulation of age-friendly goals and their implementation, based on a review of age-friendly projects and reflections on the journey towards age friendliness in one state (Rhode Island). The authors conducted a comprehensive investigation of the relevant literature on previous age-friendly initiatives, which included case studies of individual projects, meta-analyses of age-friendly work, and educational toolkits for promoting age-friendly community. They also collected original data from ten focus groups with older adults, interviews with key informant service providers, surveys of older adults and observational environmental audits. Through this multi-faceted approach, they identified recurrent questions often not overtly addressed in building livable communities, despite their being central to decisions made in age-friendly projects. This paper focuses on six questions: Age friendliness for whom? Older adults viewed as a burden or a benefit? Age friendliness by or for older adults? Is age friendliness affordable? Should the target be the aged overall or the needy aged in particular? Should interventions aim to change people or places? The Aging in Community Report, (prepared by the authors and submitted to Rhode Island’s General Assembly), reflected decisions made—albeit sometimes inadvertently—in response to these questions. It showed that priority was given to age friendliness over livability, assistance to vulnerable, older adults was given precedence over helping the entire older population, and top-down interventions were emphasized more than grass-roots endeavors. Its recommendations were geared to leveraging or modestly increasing existing resources to better serve older adults and enhancing opportunities for older adults to contribute to their community. Following the release of the report, the focus shifted from modifications of the environment to facilitating changes in individual behavior to optimize person-environment fit.