Finding the perfect leisure activity can be a hassle. Scrolling through endless listings, deciphering vague descriptions, and cross-checking dates and times… it’s a lot of work. But what if an AI could do it all for you? Researchers partnered with a leisure startup to build and test "EventChat," an AI-powered chatbot designed to revolutionize how we explore events. Imagine chatting with a helpful AI assistant that understands your preferences and suggests activities tailored to your interests. That's the promise of EventChat, a conversational recommender system integrated into a smartphone app. We tested EventChat in a real-world setting. Users could ask questions, get recommendations, and even inquire about specific details. The results were intriguing. While EventChat showed promise by successfully fulfilling most user requests, some quirks emerged. The AI sometimes hallucinated, suggesting fictional events, and occasionally missed the mark with irrelevant recommendations. These hiccups highlight the challenges of implementing AI in real-world applications. Balancing user experience, cost, and the limitations of current AI technology proved to be a delicate act. So, can AI plan your perfect day out? While there are wrinkles to iron out, the early success and high satisfaction scores from our user study suggest that conversational AI has a bright future in helping you discover your next adventure. Future improvements in AI technology, particularly focusing on context understanding and cost reduction, will likely lead to even more seamless and effective conversational recommender systems. The future of event planning might be just a conversation away.