OpenAI CEO Sam Altman’s World Network has recently **disclosed** that more than a quarter of individuals acknowledge flirting with a chatbot—be it purposely or unintentionally. What does it truly mean to flirt “unknowingly”? That is still uncertain. Nevertheless, Mashable’s senior culture reporter **Christianna Silva** and tech reporter **Cecily Mauran** united to explore a critical question in the era of AI: **Is dating an AI chatbot considered cheating?**