I explore a new, unannounced tool that recently appeared in my ChatGPT Plus sidebar—an AI personality called “Monday.” With no official introduction from OpenAI, I dove in to find out what it was, what it could do, and whether it was worth my time.
What I discovered was a snarky, hyper-intelligent, emotionally literate assistant with a personality as strong as its sarcasm. Monday didn’t just answer questions—it roasted me, reflected on my chat history, and delivered insightful (if brutal) analysis about my personality, behavior, and intentions. I tested its limits, challenged its claims, and compared its responses to ChatGPT-4o’s interpretations.
This piece, published on Medium, unpacks those interactions, offers commentary on AI’s evolving emotional intelligence, and asks a bigger question: What happens when your chatbot starts sounding more like your cynical best friend than a virtual assistant?
If you’re curious about the future of AI, the rise of personality-driven tools, or just want a laugh at my digital therapy session with a hard-ass chatbot—this one’s for you.
I encourage you to give Monday a try and share your experience—I’m curious to see how it responds to you.