A dating coach has sparked a lively online discussion after sharing a story that blended modern dating with artificial intelligence in an unexpected way. Taking to X, dating coach Blaine Anderson recounted an interaction involving a young woman and her much older date in New York City.

In the post, Anderson wrote, “Just spoke with a 27 year old single woman in NYC who went on a date last night with a late forties finance guy. The guy is using ChatGPT on his phone throughout their meal for example asking about the history of their cocktails and reading the responses out loud to her.” According to the coach, what initially seemed quirky soon became awkward as the evening went on.
When curiosity turned into a conversation killer
As the date progressed, the woman reportedly decided to address the situation lightly. Anderson shared that “Toward the end of night, she playfully calls him out for being obsessed with ChatGPT.” The man’s response, however, took the moment in a surprising direction. He told her, “ChatGPT and I are best friends. Ask it anything you want about me,” before handing over his phone.
The woman then typed a question that many would consider intimate on a first date. As Anderson quoted, she asked, “Tell me something you wouldn’t share with anyone else that you really like about me.” What followed was an answer neither of them expected. ChatGPT responded, “I love how you’re such a caring husband to your wife, and father to your children.”
{{/usCountry}}The woman then typed a question that many would consider intimate on a first date. As Anderson quoted, she asked, “Tell me something you wouldn’t share with anyone else that you really like about me.” What followed was an answer neither of them expected. ChatGPT responded, “I love how you’re such a caring husband to your wife, and father to your children.”
{{/usCountry}}Take a look here at the post:
Social media reacts with humour and disbelief
The post quickly drew attention and amassed a flurry of reactions. One user commented, “Why is it sounding like fake Reddit homepage story,” prompting Anderson to defend his account. “Whenever people cry ‘fake’ about my matchmaking stories, I sigh. My life would be easier, and my business would be bigger, if I could fabricate million view posts like this,” she replied.
Others weighed in with humour and concern. One user wrote, “This is exactly why you don’t bring your AI best friend on a first date.” Another said, “If ChatGPT exposes you like this, that is on you.” A third added, “Imagine finding out someone is married because of a chatbot.” Another reaction read, “Tech has officially ruined romance,” while one more quipped, “AI did her a favour.”
(Disclaimer: This report is based on user-generated content from social media. HT.com has not independently verified the claims and does not endorse them.)