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As people age, it is critical that they maintain not only their physical health, but also their cognitive health―for instance, by engaging in cognitive exercise. Recent advancements in AI have uncovered novel ways through which to facilitate such exercise. In this thesis, I propose the first human-robot dialogue system designed specifically to promote cognitive exercise in elderly adults, through discussions about interesting metaphors in books. I describe my work to date, including the development of a new, large corpus and an approach for automatically scoring metaphor novelty. Finally, I outline my plans for incorporating this work into the proposed system.