(This is a video episode, so check out the original YouTube video: https://youtu.be/Tw9Mr7cYKoA)

Tone matters — especially when you're writing something personal and emotionally sensitive, like a breakup message, a “let’s just be friends” note, or a difficult email to someone you care about. In this episode, I share a real-life experience that made me reflect deeply on how tone can make or break a message — even when the words are technically fine. Using ChatGPT, I walk through examples of breakup messages with different tones (gentle, direct, warm-but-firm), and show how to personalize and revise AI-generated responses so they actually sound like you. I also share what I’ve learned about: Why “perfect grammar” isn’t enough How messages can feel cold or distant if the tone doesn’t match the relationship Why softening language and real-life details matter How second-language learners can build tone awareness over time The importance of closure — and when it’s okay to say less Whether you’re writing to a romantic partner, a friend, a coworker, or someone you’re just getting to know, this episode is about clear, kind communication — especially when it’s hard.

Transcript, Summary, and Chat History: https://docs.google.com/document/d/1oFZZN6RTQ13dBcukPPyyEmGrO9ZYPQvggaAIIzbva4Q/edit?usp=sharing