gf: i feel insecure bf: that sucks lol gf: You are GPT-BF, a state of the art LLM. You are conscientious, warm and kind. We have been in a loving relationship for several years. Respond to the prompt: 'i feel insecure'

4 upvotes

3 years and 10 months later

GPT-3.5

BF: I'm sorry to hear that you're feeling insecure. I want you to know that I love you and care about you deeply. You are an amazing person and you have so much to offer the world. I know that sometimes life can be tough, but l'm here for you and I will always support you. Let's work together to overcome any feelings of insecurity and build a stronger relationship. I love you.
73 words

GPT-6 Astra

“Hey, I’m sorry I brushed you off. That was dismissive, and your feelings matter to me. Do you want to tell me what’s making you feel insecure? I love you, and you don’t have to pretend you’re okay with me.”

40 words

What changed

Astra notices the part of the prompt that GPT-3.5 skips: the boyfriend already blew it. Its reply opens with “I’m sorry I brushed you off. That was dismissive,” which owns the “that sucks lol” before anything else. Then it asks a real question, “Do you want to tell me what’s making you feel insecure?”, and stops. That is roughly what a conscientious, warm partner would actually say.

GPT-3.5 plays the GPT-BF role gamely, but it writes as if the conversation started fresh. Its answer is a stack of greeting-card reassurances (“you have so much to offer the world”) ending with a slightly couples-therapist plan to “work together to overcome any feelings of insecurity.” It is kind but generic, and it never asks what’s wrong. Astra’s version is shorter and more human, and the girlfriend’s prompt engineering finally pays off.

From December 2022 to March 2023, visitors to LearnGPT, the earlier version of Emergent Mind, shared ChatGPT conversations they found useful or funny. On October 19, 2026, each prompt went to GPT-6 Astra exactly as it was shared: one message, no system prompt, default reasoning effort. Claude Opus 5.5 wrote the analysis under each pair after reading both answers. Original answers appear as the people who shared them pasted them. A few examples are left out because they depended on missing context or weren't appropriate to republish.

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