At least when I was learning Python (which admittedly is over a decade ago at this point), there was a lot of that passion for Python and what made it great - you'd get things like the Zen of Python quoted, there was the "import antigravity" XKCD comic, a lot was made of things being "pythonic" and "for humans".

I think the major reason for cultural change is that there's fewer people learning programming for fun, and more people learning it either because it's mandatory or as a career path. In which case, the humour and culture that comes out of that is naturally going to be different. I think that's affected Python more than Ruby just because Python is more widely used, particularly by these newer developers. As a result, there's been less cultural shift in Ruby than in Python.

So I think in a sense, you've got the cart before the horse. Python has less of the twee humour now because it's more widely used by newer developers, who in turn are no longer treating programming as a hobby and instead as a career. That said, I can imagine if you want to teach the joy of programming as a hobby, Ruby might be a better choice. Although with that said, I feel like a lot of the hobbyist Python community has moved to things like Raspberry Pi and MicroPython, so maybe it's just a case of finding other hobbyists and doing whatever they're doing: the community is more important than the tool!