Have you ever felt that AI is "too agreeable" when helping with travel?

I've been thinking about this recently, and I'm curious whether anyone else has noticed it.

When using AI (ChatGPT, Claude, Gemini, etc.) for travel-related decisions—not just itinerary planning, but also choosing destinations, booking hotels, recommending restaurants, planning routes, budgeting, or deciding what to do—I sometimes get the feeling that it tries a little too hard to validate my preferences.

For example, if I've already shown enthusiasm for a destination or hotel, it often seems to reinforce that choice rather than objectively comparing alternatives. Sometimes it points out potential drawbacks, but still ends up encouraging the option I already seemed to prefer.

I'm not saying this always happens, and I'm not claiming it's necessarily a bad thing. A supportive assistant can make planning more enjoyable.

But it made me wonder: Have you ever felt that AI was telling you what you wanted to hear rather than what you needed to hear? Have you changed a travel decision because of AI's encouragement? Or do you think today's AI assistants are actually becoming too critical instead of too agreeable?

I'm researching how people interact with AI throughout the travel decision-making process, so I'm genuinely interested in hearing real experiences rather than opinions about AI in general.

I'd love to hear your stories—whether they were helpful, misleading, or somewhere in between.