When I ask Copilot something, the response usually starts with “Great question!”, followed by emojis and encouraging words that gently pet my fragile ego. Pretty much anything seems to pass for a “good question”, so if my questions are able to surpass that exceedingly low standard, I no longer feel very confident about their quality.

Don't mistake AI for someone. AI is just computer code trying to mimic understanding and empathy. There is no one behind AI but a vast emptiness and imho a rather poorly devised mirror made out of random shreds of knowledge.

Am I the only one feeling this way? Anyone else noticing how excessive encouragement can have the opposite effect?

That's 100% normal imho, it's your brain/gut feeling letting you know something is not as it should be. You should not rely on AI to feel 'validated'. As a matter of fact, you should not rely on anything and probably on that many actual persons. Only the ones you truly care about.

How do you feel when discussing with a real person, someone that won't feel obligated to be flattering... like I am not ;)