Sometimes the best advice doesn’t come from friends, family, or even a relationship coach — it comes from an AI chatbot at 11 PM. That’s exactly what one Reddit user discovered when he found himself confused about a budding romance. What started as a late-night experiment with ChatGPT turned into an eye-opening lesson on communication, empathy, and how to actually show up for someone you like.
The user shared that he had been talking to a colleague for a few weeks, and things were going well. They were grabbing coffee, texting throughout the day, and laughing together — all the classic signs of interest. But then, out of nowhere, she seemed distant. Unsure of what had gone wrong, he did what most wouldn’t even think to do: he asked ChatGPT for help.
What dating advice did he get?
At first, he expected the usual generic advice about communication. Instead, the chatbot asked him a simple but striking question: in his recent conversations, how often had he asked about her day versus talking about his own? The realisation hit him — he’d been so focused on sharing stories and trying to impress her that he hadn’t really taken the time to listen.
ChatGPT then pointed out specific moments he had overlooked. She once mentioned a big presentation at work — he never followed up. She had opened up about her sister being stressed — his only response was “that sucks” before steering the conversation back to himself. Piece by piece, it became clear he wasn’t really engaging with her world at all.
How did his relationship improve?
That realisation was enough to spark a change. The very next morning, he texted her asking how the presentation went and checked in about her sister. Her response was instant and warm. Suddenly, their conversation flowed better than it had in weeks, and the connection that had felt shaky came back stronger.
The user admitted he couldn’t believe it took an AI to make him realise what should have been obvious — that showing genuine care matters more than witty jokes or impressive stories. In his own words, it was the best dating advice he’d ever gotten, and it shifted the way he looks at relationships altogether.
Internet reacts
One user shared that, in the long run, mindfulness exercises could be beneficial for everyone. Another pointed out that ChatGPT’s emotional intelligence is often underrated. Someone else explained that while it’s not a substitute for friends, family, religion, or professional mental health care, it has become an indispensable tool for venting without feeling like they’re burdening real people.
The user shared that he had been talking to a colleague for a few weeks, and things were going well. They were grabbing coffee, texting throughout the day, and laughing together — all the classic signs of interest. But then, out of nowhere, she seemed distant. Unsure of what had gone wrong, he did what most wouldn’t even think to do: he asked ChatGPT for help.
What dating advice did he get?
At first, he expected the usual generic advice about communication. Instead, the chatbot asked him a simple but striking question: in his recent conversations, how often had he asked about her day versus talking about his own? The realisation hit him — he’d been so focused on sharing stories and trying to impress her that he hadn’t really taken the time to listen.
ChatGPT then pointed out specific moments he had overlooked. She once mentioned a big presentation at work — he never followed up. She had opened up about her sister being stressed — his only response was “that sucks” before steering the conversation back to himself. Piece by piece, it became clear he wasn’t really engaging with her world at all.
How did his relationship improve?
That realisation was enough to spark a change. The very next morning, he texted her asking how the presentation went and checked in about her sister. Her response was instant and warm. Suddenly, their conversation flowed better than it had in weeks, and the connection that had felt shaky came back stronger.
The user admitted he couldn’t believe it took an AI to make him realise what should have been obvious — that showing genuine care matters more than witty jokes or impressive stories. In his own words, it was the best dating advice he’d ever gotten, and it shifted the way he looks at relationships altogether.
Internet reacts
One user shared that, in the long run, mindfulness exercises could be beneficial for everyone. Another pointed out that ChatGPT’s emotional intelligence is often underrated. Someone else explained that while it’s not a substitute for friends, family, religion, or professional mental health care, it has become an indispensable tool for venting without feeling like they’re burdening real people.
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