The first half of this article explores how artworks can come to acquire “rich meaning” within individuals. While much previous research has focused on relating diversity in aesthetic responses to interindividual differences, this article introduces two emerging directions that extend this line of work, illustrated with recent empirical examples. One concerns understanding response diversity in a more expansive manner by adopting multi-dimensional indicators and process-based accounts, rather than reducing appreciation to a single evaluative dimension at a single point in time. The other focuses on intraindividual processes through which meanings accumulate and become layered over time, as artworks are repeatedly encountered under varying everyday contexts. The latter half turns to a different question: how experiences related to art may enrich everyday life itself. Drawing on John Dewey’s critique of dualisms that separate ends and means, and connecting this perspective with cognitive-scientific frameworks such as spontaneous thought and problem finding, the article proposes a view of “rich experience” as a process in which exploration supports the ongoing generation of aims. From this perspective, art is positioned as a particularly powerful resource for broadening exploratory activity and for fostering aim-generative ways of living.