People aren’t stupid, by and large. (They may talk stupidly. They may act stupidly. But they can actually see things. They just sometimes ignore that before talking or acting.) And yes, they can tell when the “praise” and “encouragement” they get is hollow and pointless. You don’t even have to look at the obsequious degenerative AI slop to find this. You can go back to all the late-'80s to early-'90s crap with participation trophies/certificates and “everyone’s a winner”.

When I started in school, it was really hard to get recognized. It took a lot of work and those who got recognized for it had a sense of genuine accomplishment. They had genuine self-esteem. But there’s that word: self-esteem. Self-esteem is very important, make no mistake, but unfortunately it’s not something that can be easily codified or built up in people. Institutions can’t stand complex problems with complex solutions, so they went the easy way. They started handing out trophies and certificates to everybody. Sure some of them might be marked “first place” or such (though often, as this trend became entrenched, they didn’t even get labelled with that much; people would be announced as first place, but the trophy was a generic “I attended” variety), but everybody had a trophy or, increasingly, just a certificate. (And of course since they now had to hand out dozens of trophies where before they’d only hand out a few, the trophies dropped in quality to generic, plastic, chrome-plated crap and the certificates were placed in low-grade plastic holders that would warp in three weeks.)

And a weird thing happened.

Because the people who “won” a trophy for being there knew this wasn’t any meaningful celebration. OK, maybe the first couple of times they were happy about it, but it didn’t last long and pretty soon trophies, certificates, and other forms of “recognition” got viewed as more junk. That “self-esteem” wasn’t building in those who lacked it, but those who actually worked hard for recognition certainly lost theirs. “The trees [were] all kept equal by hatchet, axe, and saw.” Because genuine self-esteem comes from genuine effort leading to genuine accomplishment and authentic recognition. And we’re very good at spotting the inauthentic.

So bringing it back around to that AI and your question, yes, excessive encouragement can have the opposite effect if it comes across as inauthentic and patronizing. The nauseating obsequiousness of AIs is one of their more off-putting features for “normal” people, and it does active harm to people who have serious self-esteem issues, either tanking them further or puffing it up to the point of delusion.