Groom-to-be claims Booking.com's AI chatbot backed £1,500 villa scam that nearly ruined his dream proposal

A groom-to-be claims his dream engagement trip to Italy was plunged into chaos after Booking.com's AI chatbot allegedly reassured him that a £1,500 villa payment was legitimate – only for the property to disappear.

Sales project manager Alfie Learmouth, 27, had planned a romantic five-day getaway to Positano on the Amalfi Coast with his girlfriend of nine years, Jordan Bland, 27, in September. But just before they were due to leave, Alfie received a message from their villa host demanding the full balance by bank transfer.

Fearing a scam, he turned to Booking.com's AI Trip Support chatbot, Dot, for reassurance. The bot, which introduced itself as 'still learning', reportedly told him the property required full payment by bank transfer before arrival.

Trusting the response, Alfie sent the money. Then, just an hour before leaving for the airport, disaster struck. The host claimed a burst pipe had flooded the property and they could no longer stay.

“It was absolutely horrendous and one of the most stressful things you could ever go through,” Alfie, from Bexley, south-east London, said. He contacted Booking.com and scrambled to find alternative accommodation. Although the company agreed to help cover the replacement stay, the nightmare was far from over.

After landing at Naples Airport, the couple discovered their luggage had not made the flight. They say they spent around £500 replacing clothes and essentials, with a further £75 taxi journey to a shopping mall.

Their first day was swallowed up by airport trips and emergency shopping. Worse still, when they tried to track down the original villa, Alfie claims it simply did not exist. A restaurant owner nearby allegedly told them another traveller had arrived a month earlier with the same photographs and a similar story.

Despite the chaos, Alfie had kept one crucial thing safe: the engagement ring in his hand luggage. On September 5, he proposed during a surprise boat trip, and the couple managed to enjoy the rest of their holiday.

But Alfie says the experience left him thousands of pounds out of pocket. ”I'm not asking for compensation, I'm asking for the bare minimum of my money back,” he said.

Booking.com apologised, confirmed it was processing a full refund and said the property had been removed from its platform. The company also noted that the booking confirmation specified card payment, not bank transfer.

British Airways said it had apologised and worked swiftly to resolve the baggage issue.