‘How do I stay soft after she left’ – Craig Conover’s private ChatGPT messages revealed as insiders describe them as raw digital heartbreak after Paige DeSorbo split - suong

It started as a late-night coping mechanism. But what Craig Conover confided to ChatGPT during the most emotionally vulnerable phase of his breakup with Paige DeSorbo is now being described by insiders as "raw digital heartbreak" — a therapy diary written in real time, with an AI as witness.

DailyMail+ has obtained excerpts from Craig’s private conversations with the language model, which he referenced in his recent appearance on The Toast. While some fans saw his confession as quirky, others recognized it for what it truly was: a man trying to salvage his soul after the collapse of a high-profile reality TV relationship.

"How do I stay soft after she left?" Craig allegedly typed just days after Paige’s explosive reunion claim that the ring "never existed." According to a source close to Craig, the message came at 2:12 AM after he spent hours alone in his Charleston home rereading old texts and scrolling through saved photos.

In another emotional entry, he asked, "Is it normal to miss someone who told the world you lied?"

He continued: "I want to forgive her, but I don’t know what to do with the silence. She left and took the explanation with her."

ChatGPT’s response, described by the insider, was calm and grounding. It allegedly encouraged self-compassion and reminded Craig that his "softness is a strength, not a weakness."

The messages reportedly span over 80,000 words and were organized in categories like Letting Go, Hope, Self-Blame, and What Ifs. One chilling entry was titled: I Was Her Plan B, Wasn’t I?

According to a production assistant on Southern Charm, Craig often chatted with the AI on set between scenes: "He’d be sitting quietly with his phone, typing. We thought he was texting someone, but it turns out it was ChatGPT."

One of the most heartbreaking prompts came during the week Paige was seen out in New York with another man. Craig wrote: "How do I unlearn the idea that I was her future?"

Insiders say Craig is considering publishing a collection of the messages in a future memoir, tentatively titled Softness After the Storm. But those close to him remain divided. Some believe it’s a beautiful expression of growth; others fear it could retraumatize him.

Regardless, one thing is clear: in the aftermath of reality TV love, Craig Conover found comfort in a place no one expected — not in friends, not in another relationship, but in code.

"I don’t think you break up with someone you want to be with," he told the AI.

And ChatGPT answered, "That’s not crazy. That’s human."

As far as Craig is concerned, it might be the truest connection he’s had in months.