ChatGPT Breakup: I Read My Boyfriend’s AI Chats & It Ended Our Relationship with Lindsey Hall

Save 10% on your next Fleshlight with promo code PRIVATE10 at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fleshlight.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. For the 256th episode of Private Parts Unknown, host Courtney Kocak welcomes writer and publicist Lindsey Hall, whose viral essay “I Stumbled Across My Boyfriend’s ChatGPT and It Ended Our Relationship” ignited a massive conversation about love, privacy, and AI in the modern dating landscape. In this episode, Lindsey shares the story behind the accidental discovery of her boyfriend’s ChatGPT conversations—and how reading what felt like his digital diary ultimately unraveled their relationship. We get into the ethics of snooping, what it means to outsource your emotional processing to AI, and the blurred lines between private thoughts and digital footprints in the age of supercharged technology. Lindsey also opens up about navigating vulnerability, attraction, intuition, and self-worth. For more from today's guest, Lindsey Hall: Follow Lindsey on Instagram @lindseyhallwrites

You can listen to ChatGPT Breakup: I Read My Boyfriend’s AI Chats & It Ended Our Relationship with Lindsey Hall online on Radio and Podcast. Open the player on this page to stream the available audio.

ChatGPT Breakup: I Read My Boyfriend’s AI Chats & It Ended Our Relationship with Lindsey Hall is an episode from Private Parts Unknown (FKA Reality Bytes) by Courtney Kocak.

This episode is 33:25 long.

This episode was published on Apr 22, 2026.

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