Experiencing cultural heritage is a voyage of discovery and learning, where emerging insights and serendipity play a significant role. The experience also happens in a blended personal and social context. At the broader level, engagement is longitudinal – what we learn from modern cultural experiences (daily life in our surroundings) can provide clues to analogous interests in cultural materials, and vice versa. This paper addresses richness of personal experience poses challenges and opportunities for capturing preferences in ways that support a user’s experience with cultural heritage across institutions and over time, both in the digital realm and where digital interaction blends with a physical space.