Siri is the worst with this, but instead of "cutesy", when it's failing to execute a simple command, it goes for a smarmy and sarcastic response. I'll never understand the mindset of the putative audience who its designers think this will please.
I once read that waitresses who initially come off as rude earn higher tips, but only if their mood softens throughout the meal. There seems to be something about “winning” the waitstaff over that makes diners reward them with higher tips.
IMO, it was a feature to have Siri come off as rude when her abilities and comprehension were still in development.