A couple thought they had all the travel info they needed thanks to ChatGPT. But one incomplete answer about a visa was enough to derail their entire trip…
Mery Caldass, a Spanish influencer and content creator with thousands of followers, was planning a romantic trip to Puerto Rico with her partner. Like many travelers in the digital age, she wanted to save time and skip the tedious research by asking her questions directly to ChatGPT. Her goal was simple: find out if they needed a visa before traveling.
According to her, the answer seemed clear: no visa was required to enter Puerto Rico. What the AI didn’t mention, however, was that “no visa” didn’t mean “no paperwork at all.” An ESTA, the Electronic System for Travel Authorization required for citizens of countries in the U.S. Visa Waiver Program, had to be obtained online before departure.
Confident everything was in order, the couple bought their plane tickets, booked their lodging, and planned activities, all under the impression that they were set to go.
It wasn’t until check-in, just hours before their flight, that reality hit: without a valid ESTA, they couldn’t board.
Emotional reaction against ChatGPT caught on camera and shared
In a video posted yesterday on TikTok, Mery appears in tears, walking through the airport right after being denied boarding to Puerto Rico. Her partner, Alejandro Cid, is by her side trying to comfort her, while she speaks directly to the camera.
“Listen, I always do a lot of research, but I asked ChatGPT and they said no,” she explains, referring to her question about whether she needed a visa to enter the Caribbean island.
The tension is obvious, quickly turning into outright anger toward the AI tool: “I don’t trust that son of a b**** anymore,” she adds, clearly frustrated.
Between sobs, Mery tries some dark humor, accusing ChatGPT of giving her bad information as revenge: “I don’t trust him anymore because sometimes I insult him, call him a jerk, tell him he’s useless, but keep me informed… it’s his revenge.”
The video racked up several million views, with mixed reactions in the comments. Some openly mocked the couple for relying on ChatGPT instead of checking official sources.
“Well, natural selection, I guess. If you’re about to take a transoceanic trip and you rely entirely on ChatGPT for advice, you’re probably not going to get very far,” one user wrote.
Others defended the AI, pointing out that the answer wasn’t technically wrong, the couple may have simply asked the wrong question about travel documents for Puerto Rico.
Why ESTA is required for Puerto Rico?
Saying “no visa is needed” isn’t wrong… but it’s incomplete, and that small gap in information was enough to ruin the couple’s trip.
Puerto Rico is an unincorporated U.S. territory. While it has its own distinct culture and identity, it follows the same immigration rules as the U.S. mainland.
- Spanish and other European nationals can travel without a traditional visa under the U.S. Visa Waiver Program (VWP).
- However, this program still requires travelers to apply for an Electronic System for Travel Authorization (ESTA) before departure.
- ESTA is mandatory even if the trip is only to Puerto Rico and does not involve entering the U.S. mainland.
- Without an approved ESTA, airlines will deny boarding, since entry into U.S. territory would be illegal.
The limits of ChatGPT for official procedures
Chatbots like ChatGPT can deliver quick answers, but they can’t guarantee accuracy — especially in areas where regulations change frequently.
Visa rules, border requirements, and customs procedures are constantly evolving. The only reliable sources are official government websites (like the ESTA website or an embassy), or outlets like VisasNews (😊).
In this case, the confusion between “no visa required” and “ESTA required” had serious financial and emotional consequences.
This isn’t an isolated incident. It underscores a key point: AI is a tool, not a legal authority. For any trip involving official travel documents, it’s essential to double-check with official sources, especially when visas or entry authorizations are involved.
