Interrogating AI: Characterizing Emergent Playful Interactions with ChatGPT

In an era of AI's growing capabilities and influences, recent advancements are reshaping HCI and CSCW's view of AI. Playful interactions emerged as an important way for users to make sense of the ever-changing AI technologies, yet remained underexamined. We target this gap by investigating playful interactions exhibited by users of a popular AI technology, ChatGPT. Through a thematic analysis of 372 user-generated posts on the ChatGPT subreddit, we found that more than half (54\%) of user discourse revolved around playful interactions. The analysis further allowed us to construct a preliminary framework to describe these interactions, categorizing them into six types: reflecting, jesting, imitating, challenging, tricking, and contriving; each included sub-categories. This study contributes to HCI and CSCW by identifying the diverse ways users engage in playful interactions with AI. It examines how these interactions can help users understand AI's agency, shape human-AI relationships, and provide insights for designing AI systems.