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> I actually from a less technical person's perspective, "cute" error messages humanize errors, showing them that there was indeed someone who made that page they are currently on and not just some soulless computer and thus making solving the problem much more approachable!

Yeah, I don't have any problem with "cute" error messages as long as they also contain all the info someone would need to identify the problem and if possible solve it. it's not the "cute" that's the problem really, it's the frustration and the lack of direction that usually comes with them.