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One of the key challenges for smart technologies deployed in this context is the development and maintenance of long-term user engagement and adoption, which is often addressed by attempting to closely mimic human social interactions. However, the more human-like the system, the more glaring fault conditions become, and the more jarring they are for users. In this study we explore the effectiveness of an alternative conversational strategy meant to encourage users to engage in positive reflection and introspection. We detail the iterative design and implementation of a prototype CA developed to engage in social conversation with older adults on selected topics of interest. We then use this system as part of a multi-method approach to investigate the effect of deliberate positivity as a conversational strategy, including its impact on user impressions and willingness to continue using the CA. Our results from different approaches, including methods such as psycholinguistic analysis, user self-report, and researcher-based coding, paint a promising picture of this conversational design. We show that the deliberate encouragement by a CA of positive conversation and reflection in users has a measurable positive impact on both user enjoyment and desire to continue engaging with a system. We further demonstrate how some user characteristics may amplify this effect, and discuss the implications of these results for the design and testing of future conversational systems for older adults.<\/jats:p>","DOI":"10.1145\/3725738","type":"journal-article","created":{"date-parts":[[2025,3,27]],"date-time":"2025-03-27T11:52:56Z","timestamp":1743076376000},"page":"1-40","update-policy":"https:\/\/doi.org\/10.1145\/crossmark-policy","source":"Crossref","is-referenced-by-count":2,"title":["What Are You Looking Forward to? 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