A growing body of research testifies to the capacity for archaeological and other cultural heritage sites to generate wonder, attachment, personal transformation and restoration, family bonding and community building amongst their visitors. Using evaluation data from two related European Commission‐funded research projects, CHESS and EMOTIVE, we discuss here our work in developing mobile-based emotionally‐engaging digital stories for visitors to diverse cultural heritage sites. The sites range from world-renowned museums, such as the Acropolis Museum in Athens (Greece), to UNESCO World Heritage sites, such as the Çatalhöyük Neolithic archeological site (in Turkey). The evaluation studies feature detailed observations of visitors on‐site as well as post‐experience questionnaires and interviews, providing us with rich data on several axes; e.g. in relation to interactive story plot and narration, staging and wayfinding in the physical space, personalisation and social interaction. In this chapter, we specifically focus on shared experience and the impact that digital technology can have in promoting the cultural site as a social space. On the one hand, our findings testify that digital empathic stories can evoke narrative transportation, and even, in some cases, personal attachment and critical (self‐)reflection, which leads us to consider how their enchanting capacities might be pushed even further into the building of broader, collective social conscience. At the same time, the findings reveal the challenges, both conceptual and practical, of designing a shared digital experience in which visitors engage with the site and each other in meaningful ways