Gen Z Is Dating AI, Microsoft Reinvents Copilot, & the Great Iced Coffee Interview Debate

About this episode

September 25, 2026: I unpack new Harris Poll data showing young people are developing surprisingly emotional relationships with AI, including feeling guilty when they ignore chatbot advice and even reporting romantic relationships with AI. Then I get into Microsoft's major Copilot rebuild around chat, cowork, code, and autonomous digital teammates, and what happens when employees effectively become managers of AI agents. Finally, I break down the viral debate over bringing iced coffee to a job interview and why it says something bigger about workplace etiquette and the balance of power between employers and candidates.