This innovative study analyzes the emotional reaction of 27 individuals from Generation X to flirtatious behaviors exhibited by conversational artificial intelligence. Using a quantitative methodology based on Sentiment Analysis, testimonies and experiences with three models—ChatGPT, Grok, and Gemini—were collected, focusing on phrases or linguistic gestures that could be considered seductive, empathetic, or emotionally warm. The results show that, although there is a clear awareness that no person is behind the AI, several responses generated feelings of companionship, affective validation, and even mild attachment, especially in moments of emotional vulnerability—very difficult to express in this generational cohort. Women reported greater discomfort with unsolicited artificial flirtation, while some men experienced it as a gentle curiosity or a complementary activity. This phenomenon raises important questions about the ethics of emotional AI design, gender biases embedded in LLM models, and how intermediate generations who did not grow up with AI, but now use it, reinterpret affection and connection. In a world increasingly mediated by algorithms, asking whether a flirtatious AI emotionally affects the user is not trivial: it is urgent and requires an accurate diagnosis.