Though beloved for its nostalgic charm, the traditional arcade industry is being taken over by mobile gaming and virtual reality due to outdated technology. Imagine if the conventional arcade system combines with the modern technology of chatbots in the form of a retro gaming console, the Gameboy. This research investigates Arcadio, a Gameboy-inspired chatbot that leverages conversational AI to modernise the arcade setting. This paper explores the conceptual system behind Arcadio’s design and focuses on streamlined payments, instant machine alerts, and multiplayer social interaction in arcades. Drawing on customer feedback, key industry challenges, and real-world implementation data, the research evaluates the effectiveness of Arcadio in rebranding the arcade industry and attracting a new generation of arcade enthusiasts, thereby improving the overall arcade and customer experience.