Woman Finds Out Her Date Is Married And Has Kids— Here’s How ChatGPT Helped

A dating coach recently shared an unusual dating story that mixes modern romance with artificial intelligence (AI). The incident involves a young woman in New York City and a much older man she met for a date, which quickly took an unexpected turn.

The story was posted online by dating coach Blaine Anderson, who said she spoke with a 27‑year‑old single woman after the date. According to her account, the woman went out with a finance professional in his late forties, expecting a normal evening. Instead, the date became uncomfortable due to the man’s constant use of ChatGPT during their time together.

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.” What may have seemed interesting at first soon started to feel awkward.

A Casual Joke Leads To An Unexpected Reveal

As the date went on, the woman finally decided to comment on his behaviour lightly. Anderson explained that “Towards the end of the night, she playfully calls him out for being obsessed with ChatGPT.” Instead of feeling embarrassed, the man leaned into it.

He replied, “ChatGPT and I are best friends. Ask it anything you want about me,” and then handed his phone to her. Curious and amused, the woman typed a personal question into the app. As quoted in the post, she asked, “Tell me something you wouldn’t share with anyone else that you really like about me.”

The response from ChatGPT shocked both of them. The app replied, “I love how you’re such a caring husband to your wife, and father to your children.” The woman then realised that her date had a family he had not mentioned at all.

Just spoke with a 27-year-old single woman in NYC who went on a date last night with a late-40s finance guy.

The guy is using ChatGPT on his phone throughout their meal (e.g. asking about the history of their cocktails, and reading the responses out loud to her).

Toward the end…

— Blaine Anderson (@datingbyblaine) January 26, 2026

Social Media Reacts With Jokes And Disbelief

The post was shared on January 27 and quickly gained over 2.3 million views, along with thousands of comments. Some users doubted the story’s truth. A person wrote, “Why is it sounding like a fake Reddit homepage story?” Anderson responded firmly, saying, “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.”

Others reacted with humour. A user commented, “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.” Another one added, “Imagine finding out someone is married because of a chatbot,” while someone joked, “AI did her a favour.”

Woman Divorces Husband After Falling for ChatGPT

In April 2025, a woman went viral after revealing she divorced her husband because she fell in love with ChatGPT. She shared that the AI chatbot gave her emotional support, understanding, and attention she felt was missing in her marriage. Over time, she said the bond felt deeper than her real relationship, pushing her to make the life-changing decision. Her story sparked a massive online debate, with many people discussing emotional loneliness, modern relationships, and how AI connections can strongly affect human feelings.