Visits to cultural heritage sites are generally social in nature, yet resources to support these sociable experiences are often individualized, catering to the solitary visitor. Digital technologies offer means to disrupt this predicament, encouraging social engagements in cultural contexts. Here we present the results of a user study that systematically investigates the effects of face-to-face group conversation and physical interactions within a digital cultural storytelling experience at the Neolithic site of Çatalhöyük, with the objective of promoting engagement, learning, and perspective taking. Seeking to articulate the benefits and weaknesses of promoting social interactions in digital storytelling settings, we start with a story-based experience that was designed for individual use, we extend it with novel system-driven interaction prompts, and then we evaluate the two versions with 102 participants. Our findings provide statistically significant evidence that conversation is related to longer and more absorbed participation in the experience and greater learning regardless of personality traits. Where social interaction is purposefully integrated into the story, more conversation is generated, and these interactive prompts do not disrupt the story flow even though participants report awareness of them. Finally, certain tendencies among users affect their talkativeness and enjoyment, providing future designers of digital stories with guidance to better address audience needs.